A Letter Instead
by LilyBolt
Summary: This is a series of letters written by various characters (mainly Sam or Dean) at different points in the show. Not a slash fiction.
1. Everything

**Authors Note: This is a brief OneShot showing a letter that Sam wrote to Dean the night before Swan Song. Reviews are very welcome! :D **

_Dean,_

_ I'm not really sure what to say to you, so I'm writing you a letter instead. Of course the problem is that I can't think of what to write either. What do you put in a letter to your brother before you say yes to the devil and trick him back into Hell's dungeon? How do you say goodbye? I guess that's the goal here. To say goodbye, and somehow convey to you all of my gratitude for everything you've done for me. _

_ I know it was never easy. I know that you gave up everything for me since I was little. Food, sleep, comfort. Everything. I remember when I was three, and you used to stay up into the early morning hours keeping watch before dad would get back from a hunt. You were only seven, and you never complained. Not once. Did you know, I used to think that when I was seven I wouldn't be able to sleep much anymore, because I thought that kind of thing was normal? And then when I turned seven, I guess I gave you a pretty rough go about bedtime, because I couldn't figure out why you got to stay up and I had to sleep. _

_ I remember my first day of high school, and I was nervous because I was small, and new, and probably going to be leaving the school in a few weeks anyway, so I didn't even have a motivation to try and fit in properly. And I remember, I didn't have to tell you I was scared. You just knew, and then you gave me that talk. I don't know if you remember it, but I do. You told me "High school is nothing. You've seen and done more than most of these kids will ever experience, and if their lives were in danger, you'd be the one who could save them. They're a bunch of boys, but you're a young man Sammy." It was the first time anyone had told me I was a young man. I know it sounds stupid, but it meant the world to me. Dad had never looked at me that way, but you were looking at me all proud and approving. I survived that whole semester based solely on your words. On your faith in me._

_ You've always had faith in me too. Even when it was pretty clear you shouldn't. Thank you for not shooting me when Meg possessed me. Thank you for coming back for me, even after I took up with Ruby, punched you in the face, and called you weak. Thanks for choosing to let me back in, after I betrayed you. And thanks for selling your soul for me. It just hit me I never really said that to you did I? I was too busy being worried and sad, I never actually thanked you. For being willing to sacrifice literally everything to save me. Well, thanks. For…for everything. _

_ But now I'm asking for something you won't want to give, and I know it. I am asking for you to keep going, after I take this giant leap. Dean, I'm begging you. Don't give up. Go fix cars, and find love, and have a family. Go be amazing, just not at hunting. Go experience life at its best. Do that for me. Because you have given so much. Given me everything. I know it's hard, but I am trying to give you something now. Promise me, Dean, that you will try. Because if I can trust that at least you're safe and maybe even happy somewhere topside, than that would mean more to me than anything. The world being safe, that's great. But you being safe? Dean, that's everything. _

_ I don't really know how to wrap this up, so I guess I'll just say thanks again. I will never forget everything you've done, and I will always love you. My big, cocky, slob of a brother, who I wouldn't trade for anything in the world. I love you man._

_Sam_

**Secondary Author's Note: This is complete for now, but I might add chapters containing letters from different times/characters later, if it looks like that would be well received.**


	2. Knew

**Author's Note: Here it is! Chapter two. :D This letter is from Dean to Sam a few months after Swan Song. Oh, and before you read, I want to take a moment to express my gratitude to missingmikey, CasterChroniclesLover, mb64, IrishNun, lilliannaelizabeth, reannablue, and Priya723 for their amazing reviews and support. I truly appreciate it, so thank you! :D 3  
**

**Disclaimer: Supernatural isn't mine. :( **

_Sammy,_

_ So, Lisa told me a diary would help me with my "repressed grief". That's what she calls it. I call it "the fact that I'm mostly dead inside", but hey, to each their own right? At any rate, I'm not going to spill my guts out to some fuzzy diary like a little girl. But I admit I need to spill them somewhere, so I'm writing you a letter instead. You wrote me a letter before you…left. I still have it. I don't know why. It's just paper, it's not you. _

_ Anyway, you'd be proud of me. I'm hitting my third month with Lisa and Ben this week, and I lead an almost respectable life now. I don't fix cars, but I build things with a construction crew. I go to work at nine and come home at five and I even drive a pick-up now. I still have Baby, of course. But I…I needed a break from her. She just feels too empty. Or when I look at her I feel empty. Or maybe it's just that I feel too much. I can't forget it all, you know? Every single time we rode in that car for ungodly amounts of hours and miles, through rain and sun and… I just can't forget it. Not really sure I want to._

_ I miss you Sammy. I miss everything about you. I miss your bitch-face and your smile. I miss the way you used to grumble whenever I dragged you to a bar. I miss when you used to tease me about my bow-legs, and the way you used to tower over me with your massive height. I miss the way you always ate salads at fast food joints, and the way you never forgot to get me pie. I miss the times we laughed and cried and fought. Yeah, I actually miss the way you used to yell at me. Because you were here. _

_ Remember when I sold my soul, and we got into that fight because I was being all nonchalant about it and kept risking my neck for fun? I was challenging fate, but you stopped me before I could go too far. I still remember it perfectly. You said you wanted me to "drop the act and just be your brother again." Those words lasted Sam. I realized in that moment that you really did care. I might not care about me, but you always would. _

_ And then I remember when I got back from Hell, and I was so mad when I figured out what you'd been up to. I got so pissed I hit you right in the mouth. I regretted it. Did I ever tell you how damn sorry I was about all of that? How I wished I had tried to be more understanding? And I regret saying I'd hunt you if I didn't know you, because it was a low blow and I was aware of that. Because if there's one thing you're not Sam, it's a monster. You're the kindest, strongest, flat-out best guy I know… Knew._

_ I didn't get to tell you this though. You jumped, and I was left sitting in that damn cemetery thinking about all the things I should have said but hadn't. And now it's too late. Now you're gone. You're gone, and I miss you so freaking much Sammy. _

_I'm gonna stop writing now, because I think Lisa was wrong. _

_Dean_

**Secondary Author's Note: Ok. I have some ideas for more of these, but I am definitely open to suggestions. They can be from any point in the series, and between any characters. Even though the first two chapters are technically sequential, the rest don't have to be. Also, these are non-slash letters (unless the slash is already established in the show) because I'm trying to keep it as authentic as I can, and because I'm no good at writing slash fiction. lol **


	3. Constant

**Author's Note: Letter number three is done! This one is for mb64, who requested (among many things I promise to do my best to get written) a letter from Sam to Dean after Sam left for Stanford. I also want to thank mb64 and lilliannaelizabeth for their speedy reviews to chapter 2, and all of you who have read and supported this so far. **

**Disclaimer: I am not the owner of Supernatural. **

_Dean,_

_ I imagine you're torn on how to feel reading this. I know you've got to be really pissed at me for leaving, but I also know you don't want to lose touch any more than I do, so in that sense I bet your glad to get this. I would have called you, but I didn't want dad to be in the room and get mad. I figure it's best to keep this contact private for now, so I'm writing you a letter instead, and sending it to Pastor Jim to give to you. _

_ I had my first week of classes. It was…weird. I like to learn, but it was the first time in a while I sat in a room learning about something that I wouldn't need to hunt later that day, and I couldn't help but expect it to turn into a monster lecture at any moment. My professors are pretty nice. I have this one woman who speaks with a really thick accent, and she does little dances and stuff to keep her students alert. It sounds strange but it's necessary, because she teaches my 8am philosophy class. And there's a guy in my government class who looks like you. He wears a big leather jacket, and has your hair cut, and even wore a Zeppelin shirt last time I saw him. Actually, that's kind of what made me want to write this. I miss you Dean. _

_ I know you feel like I betrayed you by walking out on hunting and family and all of that. I know I hurt you pretty badly. I need you to know, Dean, that it wasn't you I wanted to leave. Never you. You have always been what kept me sane in our crazy life. Whenever I was feeling overwhelmed or scared or worried, you were there. You were always there. _

_ Like that one time when dad was gone for literally three weeks straight…He left us at the motel with a little cash for groceries, and a phone so we could call him if something happened. And then something did happen. Turned our there was that spirit hanging around the motel, and you stayed up all night with me in a salt circle telling me it would be ok. And you finally reached dad, and he came and ganked the spirit, and then you and I slept for like, a whole day. I don't think I told you, but I never needed to be told it would be ok. You were there, and so I trusted that it would be fine. Dad, yeah, he'd kill the ghost, but you were safety in and of itself. No ghost could get through you. _

_ And then there was that one hunt, about a year later. You and dad went after a werewolf and you got clawed up really bad in the process. You came back all bloody and sheet white, and I freaked out inside. It was the first time I had seen you actually hurt. Not banged up, or a little scratch, but severely injured. I was only eleven, and I remember thinking you might die. You lived, but a part of me died that night. The naïve part that believed you were invincible. _

_ Because from that moment on I saw the truth. You weren't indestructible. You were determined, and selfless, and brave. (A bad combination, in a good way.) But you were still flesh and blood. I saw that you would always throw your neck out there for others, and most especially me. And over the years, as I watched you have more close calls than any guy in his late teens should experience, I couldn't help but begin to dread it. The inevitable moment where it all goes wrong. _

_ Dean, I didn't leave just because I wanted a normal life. I mean, I do want an education and a future free of constant hunting...But I also left because I can't watch when it does go wrong. When it isn't a close call, but right on the mark. Dean, I can't watch you die. _

_ I know I've told you a million times that I wish you'd quit hunting. That you could have a different life. And you always say you can't because of dad, but I know it's because of the people. You like to save people, and I respect you so much for that. But saving people risks your life basically every time. I don't want to be standing there the day some monster gets the better of you. I think it would kill me._

_ I know leaving you isn't the best way to deal with that fear. It's cowardly, and I admit it. But there's a small hopeful part of me that thinks maybe you'll see me get out and have a life, and then you'll want one for yourself. I know it's a long-shot, but it'd be great. Maybe you'll decide to hang it up, before something else takes the option away. But like I said before…I know you. I know that's about as likely as Dad suddenly showing up at Stanford to give me his blessing. _

_ So can you compromise with me? Promise me you'll be careful. Not throw yourself into things without thinking. Because you've got a great brain Dean, and you should use it. Plan ahead, exercise caution, and be safe. Because even though I left, I still need you. Even long distance, you're my constant. I might have grown up and gone off to school, but I still need my big brother. So you keep yourself safe for me. Please. _

_Love,_

_Sam_

**Secondary Author's Note: Thank you so much for reading! Reviews and requests are most welcome. :D**


	4. Not For Bringing You Back

**Author's Note: So this is for mb64, who requested a letter "from Dean to Sam while Sam was in the hospital with Lucifer in his head". This letter was written maybe a day before Dean found out about Emmanuel. I want to take a moment to thank flygirl333, mb64, lilliannaelizabeth, knwinchester, a guest by the name of sarah, and kjdw for their reviews. It is completely amazing every time I see that people are enjoying my work, and I can't thank you all enough for your support. :) **

**Disclaimer: I don't own Supernatural. :(**

_Sammy,_

_ I'm writing this letter to apologize. Not for bringing you back, but for letting you jump in the first place. Screw the world. You shouldn't have had to go to Hell for its safety. I'm sorry I let you take that leap, because I of all people should have stopped you. I know exactly how bad it gets downstairs, and yet I let you dive right in. I regret it so much Sam. I should have researched more or fought harder. I should have found a way to kill Lucifer before it got to that point. I should have let the world burn so you didn't need to. _

_ I can't stand the thought of what you went through, and every time I look at you now… all weak and tired and defeated…I can't help but think of what it must've taken to get you there. I know you're stronger than me. Always have been. Maybe it's because you're huge, but I just think it's because you're a better guy. You didn't end up trying to become like Lucifer to escape the pain. You stayed Sam, and let them destroy you without ever losing yourself like I did. I am proud of you for that. I just wish you had never gone through any of it. I wish I hadn't let you fall… Jump. Same thing. I let you down, and I regret it. _

_ But I don't regret bringing you back. Much as it kills me to see you suffering from these hallucinations, I know that to get to this point your soul had to suffer so much more in Hell. So I'm glad I got you out of there. I just wish I could've gone in your place. Why was the devil not interested in me? I'm the guy who tortured souls. Lucifer should've wanted to jump my bones, not yours. And Michael should've been all over you, mister sensitive, caring, and benevolent. Of course, that would be if angels really were the all-loving creatures on the Hallmark cards. I guess we learned that's not the case, huh? Even the nerd angels are total dicks who let you down. _

_ Have I thanked you yet for always sticking with me? I mean yeah, there was the Ruby thing, but you did come back. You came back, and you pulled me through my darkest moments. And when you had no soul, I remember it hurt just to be in the same room with you, because I missed my brother so much. I missed having that shoulder to lean on, because I don't know what to do without it. I play big strong brother, but deep inside you know there are times I need to break down. You're always the one who gets me through those times. _

_ You know I've tried every faith healer in the book, and no luck so far. I've looked up spells, rituals, everything. I've been a regular Sammy with all my research… And still no answers. Sam, what if there are no answers? What if I failed you and this time there's no fixing it? Sammy I'm so sorry… _

_ I don't know what to do. How do I fix this? I've got to fix it. Death isn't claiming you right after he brought you back. I will figure out a way to save you. I will, because I'm not losing you again. I'm not promising to build a life for myself again either. Last time, you made me promise that. Not this time Sammy. This time if you go, I go. So there's your motivation. Now get better so I can stop crying my eyes out over this letter like a girl. Please, Sammy, just be ok.  
_

_Love,_

_Dean _

**Secondary Author's Note: Thanks for reading! Reviews are appreciated, and suggestions are welcome! :)**


	5. Idjits

**Author's Note: Ok, so this one is to fulfill mb64's last request: A letter from Bobby to both guys written at any point. This is an email (close enough to a letter, right?) that Bobby wrote some time shortly after the Eve's Khan Worm. (From the episode "And Then There Were None" in season 6.) I want to pause here and thank lilliannaelizabeth, jojospn, mb64, and flygirl333 for their awesome reviews. I also want to thank all of you who have read these letters so far. You guys are all great! **

**Disclaimer: Supernatural isn't mine. :P**_  
_

_Idjits,_

_ So, this email automatically gets sent if I don't log onto my account for two weeks. So basically, when I kick the bucket. I did it this way because I figure we won't have time for goodbyes if I go the way I hope, which is "down swingin'". (I figured this after I got toasted during our run-in with Eve's pet brain-slug.) Anyway, I guess I wanted to make sure those goodbyes got said somehow, so here goes. (And so help me Dean, if you make some sly remark about me growing lady parts I will find a way to haunt your ass.) _

_First, Sam: _

_ (Dean, he's first because he's taller. Not so sly now, huh?) Sam, I want you to know that I have always been impressed by you. I know there have been times when you felt like I was ashamed of your actions. I still remember when that demon took hold of me and made me verbally disown you. That wasn't me then, and it wouldn't be me any other time either. I think you're a giant pile of "messed-up-in-the-head", but you're also the kindest man I know. Sure, you've made mistakes, but you've never once left them unresolved. So you meant well, but it went south. You know what matters? You cleaned up your damn mess, even when it cost you everything. That's a man who deserves respect. That's the man I'm proud to have known. _

_Now for you Dean:_

_ Remember that day when you came back from Hell and I hung up on your phone call, and then tried to kill you more than once when you showed up at my door? That was my way of saying I loved you. Because I was devastated when I lost you boy, and I wasn't gonna let some monster trick me into thinking you were back. Not because I cared the monster was a jack-ass, but because I didn't want the disappointment of realizing you weren't really there. So I decided to nip it in the bud. Guess I'm glad you're so quick on your feet, because I would've been really disappointed if I realized I'd just killed you right after you got back. Speaking of all that, I remember a different time when I called you a fool for selling your soul. I stand by those words. It was damn foolish. But I never was ashamed of you for it. I sometimes worry you thought I couldn't see why you made that decision. No, I understood. Even had to admire your devotion to Sam. But what I couldn't accept was the loss of one of my boys in exchange for the other… Because that's what you both are to me. My boys. _

_Back to you both: _

_ I know you've always known you're welcome at my place. I know I've made it clear I cared. But what I never really tell you is how much it means to me, having you around. You're the kids I never had. You're the two boys that I got to watch grow up, and watch movies with, and fight about stupid things with, like what weapon is best to gank a wendigo… Maybe not the most normal stuff for a family to talk about, but it never mattered to me, because we were talking. Now I know you had a daddy, and I ain't trying to replace that. But I won't deny I've loved you like my own always, and will never stop. _

_ So if you're reading this, thank you boys for everything. For dragging your stupid buts to my little corner of Sioux Falls every time you needed something, and for letting me be the grumpy old guy to give it to you. Thank you for giving me a sense of family in return for my efforts. Most importantly, thank you for being alive and healthy, and able to read this, because that's what matters to me. What has always mattered to me, and will always matter. _

_ Not sure how to end this. I guess it can end with the one thing I haven't said yet, because it feels so damn cheesy. Goodbye boys. I'll be looking down on you, all proud-like, grumbling at your idjit behavior. _

_Bobby _

**Secondary Author's Note: Ok, so I know Bobby made a joke about haunting Dean. Sorry to stab people in the feels with that, but the letter _was_ written before Bobby died, so he didn't know he would make that choice. Anyway, thank you very much for reading! Reviews and suggestions make me smile! :)** **(Oh, and jojospn, your request is coming up next!)_  
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	6. Hypocrisy

**Author's Note: This is for jojospn, who suggested "one from Sam after he finds out Dean sold his soul". I want to thank m1tchells, mb64, ClassyMuse, kjdw, jojospn, and a Guest for their awesome reviews. I also want to thank everyone who has read and supported these letters thus far. I can't put in words how awesome you all are. :)  
**

**Disclaimer: I don't own Supernatural. :P  
**

_Dean,_

_ Why did you do it man? What made you think I would be ok with that? I guess I get it. I really do, because it would kill me to lose you too. But you don't just sell your soul and expect the person you did it for to be all good with that! Because now it's me who has to lose you. I'm not letting that happen. Whatever you say about me needing to be idle through this because I'll die if I try and save you…it's crap, ok? Because you can't seriously expect me to sit on my thumbs while you get dragged off by some Hellhound. No, I'm going to do literally anything I can to save you. _

_ I know it's hypocritical of me to say that, because you were only doing everything you could to save me. The difference is that I was already dead, Dean. You're alive, and healthy, and you want me to let all of that change. Not on your life. I am grateful to have a brother who cares about me enough to go to such lengths to look out for me. But dude, does it ever occur to you that I want to do the same for you? That I would never, even in my craziest moment, ask you to sell your soul for me? That I would rather die, or stay dead, or never even have been born? _

_ You're asking me to let you go to Hell. Forever. For me. You wouldn't let me do that for you, not even in a million years! You'd kill me for trying. Well guess what, if it comes down to it, that's exactly what I'm trying. Nobody goes to Hell for me except me. And especially not you Dean. _

_ You've done everything for me my whole life. Since I was a baby, you have given more to me than anyone. If someone asked me who played the role of "father" in my life, I'd have to say my big brother did. You took me to the park and pushed me on the swing. You taught me how to walk, and talk, and read. You taught me how to ride a bike. You made sure I got the right amount of medicine whenever I was sick. You convinced dad to let me play sports that one summer. You were there at every practice, every game too. Never missed one. You taught me how to drive, and how to flirt with girls. Dean, you have been everything to me my whole life, and you want me to just give you up without a fight? _

_ I know you did it because you love me. But I love you too man. I won't stand by and watch you die. Any more than you would for me. Because even though you have a massive self-loathing complex going on, I think you're more than worth the fight. And if I die in the process, I die knowing I saved you. I think you can relate to the feeling, right? _

_ I guess we're both big hypocrites. I guess this just sucks. But I'm going to fix it. I swear, I'm going to save you. Because no matter how hypocritical it is, I'm ok with dying for you. I mean obviously the better scenario would be us both surviving. I do promise I'll strive for that version of events. But Dean, no matter what, I'm not letting it end this way. You've been the greatest brother a guy could wish for, and you don't deserve to go like this. I've got your back. I'm going to protect you for once. Because if you think saving me is your job, what do you think I believe mine is? _

_Sam_

**Secondary Author's Note: Thanks for reading! Reviews and requests are most appreciated. :)**


	7. Faith

**Author's Note: This is for mb64, who suggested "writing one from Sam to Dean when Dean was dying during 'Faith'". So, as requested, this a letter from Sam to Dean written very shortly before Sam drags Dean off to see the faith healer for the first time in 1X12. (Also, that happens to be the episode right after 'Scarecrow', which gets mentioned in this letter.)I would like to thank reannablue, kjdw, mb64, jojospn, and a Guest for their wonderful reviews. I also thank everyone who has read these so far. You guys make this whole "writing" thing completely worth while! :)  
**

**Disclaimer: I'm not the owner of the epicosity that is Supernatural. :P **

_Dean,_

_ So I don't even know where to begin with this. It's just so wrong, you know? Of all the things that could put you in the hospital, getting electrocuted was not what I'd have expected. And yes, I say "put you in the hospital" like you're going to leave it, because you are. I'm not letting you die in some hospital bed. Well, like I said to you before, I'm not letting you die period. I'm finding a way to get you fixed up. _

_ I've been looking into everything I can. Rituals, miracle workers, faith healers. You name it, I've looked it up. I found a faith healer that seems legitimate enough. I'm going to find a way to trick you into seeing him. And yeah, I know I'll have to trick you. You would never go for something like that of your own accord. You're mister "I'm too tough for prayer healing". Well, like it or not, prayer and faith seem to be our only options at this point._

_ Prayer is what I've always had. I've prayed so many times before, and you know what? It's worked. That night you got mauled by the werewolf and I was like, eleven? Yeah, I prayed so freaking hard to God that he would make sure you were ok. That you would live, and recover smoothly, and be back to picking on me within the week. He listened, because you ended up just fine. And then I remember after I ran off to Flagstaff, I prayed that if I saw you again, you wouldn't hate me for having left you. A few days later you and dad found me, and you just gave me a giant hug and told me to never run off like that again, because I'd "scared the shit" out of you. _

_ Even recently I've done it. I prayed just a few weeks ago for your safety when I went off to meet up with dad in California. I remember waiting at the bus station, and calling your phone over and over but not getting through to you. You had said you were going after that Pagan God, and then I couldn't reach you. I had this awful feeling about it. I couldn't keep chasing dad at that point, because I was too worried about you. So I took off in your direction, and the whole way back to Burkittsville, I prayed to God that I wasn't too late. I prayed that you would be alive when I found you, and unharmed, and even willing to forgive me for leaving you like that. Again, God didn't disappoint. You weren't exactly safe when I got to you, but you were alive and healthy. You even seemed happy to see me. _

_ I know it could all be written off as coincidence, or whatever. And I don't really expect you to feel the same about those times as I do. After all, you weren't the one praying, so you didn't feel it. But I can tell you, I felt it. I felt God's hand in those events. So as I am praying again to God to save you this time too, and I really believe it will work. Because God hasn't let me down so far. He reminds me of you in that way. And if he's like you, then I know he's definitely worth my faith. _

_Sam _

**Secondary Author's Note: Thank you for reading! Reviews are much appreciated, and I am always open to suggestions for new letters! :)**


	8. Proud

**Author's Note: I wrote this for ClassyMuse, who requested a letter from John to Sam after Sam left for Stanford. In my opinion, this is the letter John wrote and then never sent because he was too busy hunting. I want to take a moment and thank flygirl33, jojospn, mb64, and m1tchells for their reviews. I also want to thank everyone who has read these letters so far. You guys are the best! **

_Dear Sam,_

_ It seems like only just the other day I was watching your mother cradle you in her arms in the hospital. You were so small, but you were a bundle of energy. All noise and movement all the time. We had such a rough go getting you to sleep at night. You never did want to do as you were told. You were stubborn then, and you're stubborn now. _

_ I want you to know, I don't fault you for that characteristic. I might yell at you and get angry because you challenge my authority. That doesn't mean I don't admire your guts. You stand up for yourself, and you do what you think is best. Now, I may not always agree with your definition of "best", but I respect your determination and strength. It's hard to stand up to family, especially me. I'm not the easiest guy to deal with, and I rarely ever take the time to hear your side of the argument. I know this. _

_ I know we've had some serious fights, and have both said things we didn't mean to say. I never meant to "banish" you. When I said not to come back, I was caught up in the moment and angry and stupid. Of course I want you to come back. I know it wouldn't be permanent, and that you're in school now. That's not really what I mean by come back. But I would love a visit. Or a phone call would be great. I miss you, son. And I'm sorry I ever made you believe I wouldn't. _

_ Speaking of school and apologies, I'm sorry I didn't commend you for getting into Stanford. You were right. Most fathers hear their son got a full ride scholarship to a fancy university, and they go crazy with pride. I was an idiot, and yelled at you instead. Well, this is my chance to right that wrong. I am very proud of you. I truly am. You have a brain to rival the greatest, and I am thrilled that you never gave up on your education. After the crappy childhood I put you through? Anyone would understand if you had dropped out of school and never picked up a book again in your life. Instead, you dedicated yourself to never missing an assignment and never letting your scholastic skills get rusty. You trained your brain like I trained my body in the marines.I guess I have a hard time relating to that kind of work. Homework, and book reports, and SATs. I never understood that kind of thing and I guess that, like everything I don't understand, I reacted by hating it. I don't really hate it. I'm impressed that you have the intelligence to thrive in the scholastic world. Good for you. _

_But perhaps the most important thing I want to say, Sam, is that I don't hate you. I yell, and shout, and get drunk, and say awful things. But I never have, don't, and never will, hate you. You are my son, whether you chose to be my son in some old motel room with Dean and I, or from some dorm room at Stanford, you will always be my boy. _

_ So I am sorry for making you doubt that. For saying things I shouldn't and for not showing you more often how proud of you I really am. I hope your classes are going well. I hope you get that degree you dream of, and become the best damn lawyer the world has seen. And remember, you always have a father to turn to, even when that father acts like an ass. _

_Love,_

_John _

**Secondary Author's Note: Thank you for reading! Reviews are very welcome. I have also had many requests for different letters recently, and I promise I am working on them! They are all great, and I am always happy to get requests from readers. :)**


	9. To My Sons

**Author's Note: This is a letter from John to Sam and Dean written just before Azazel takes his soul at the hospital. In my opinion, this letter was definitely written, but of course Azazel intervened and the boys never saw it. :P This was requested by both ClassyMuse and mb64, so I hope you both like it! I want to thank jojospn, reannablue, ClassyMuse, mb64, olegnAiDociN, a Guest, and flygirl33 for their reviews and support. Also, a thank you to everyone who has read these letters. You're all amazing! :) **

**Disclaimer: I'm not the person who owns Supernatural. **

_To My Sons,_

_ First, I want to apologize. You should never have gotten stuck in the mess you're in now, and it's my fault. I lead you into a battle I didn't fully understand. I trained two young boys to be hunting machines, and then handed them the task of killing a monster I couldn't defeat on my own. It was wrong, and I'm sorry. Mary wouldn't have wanted this, and neither of you deserved this. I want you to know, you have my permission to stop. Stop being hunters, and start actually living. _

_ Because boys, I wasn't paying attention. This all stared because I lost my wife to this demon. I lost the woman I loved because this monster attacked my family. And what was my response? To run blindly after the thing, dragging my kids with me. If I had been paying attention, I would have seen how I was risking you both when I let you join the pursuit of this yellow-eyed bastard. It was stupid. I admit I wanted to have you with me because I need the strength I feel when my boys have my back. But it was selfish and dangerous. I almost got you both killed, and what would that have left me with? The death of everyone I ever loved weighing on my shoulders… _

_ I was wrong to turn you into hunters, and I was wrong to let you both take on this particular hunt. Dean, you were right. Family is always more important. Sam, thank you for not shooting me. Thank you both for proving that you're are smart enough to stop while you're ahead. Before all that remains is bodies and loss. I wasn't smart enough, but I'm fixing that now._

_ Dean, I am doing this to save you. Because if anyone deserves to be saved, it's you. Son, you have been incredible and I'm so grateful for the man you have become. You are strong, kind, and have your priorities in the right order. Again, thank you for showing me that at least one Winchester has the ability to say no to a hunt for the safety of his family. Of course you have always been the glue that held our family together. Thank you for always looking out for Sam. Thank you for always looking out for me. Thank you for being the best damn kid a crazy father could ask for. Just, thank you. _

_ Sam, I want to thank you as well. Thank you for challenging me by trying for a normal life, because in doing so you proved that at least one Winchester has the strength and motivation to escape the endless hunt that I have subjected us all to. I only ask that, when you do get out this next time, take your brother with you. Drag Dean kicking and screaming if you must, but save him from this lifestyle. I was wrong. I don't want my boys to live their lives as hunters. I want you both to go on and have families of your own, and never set foot near a vamp or werewolf or demon again. Sam, I know you can do this, so thank you for providing that source of comfort for me as I take this leap. _

_ Sons, please take this gift I'm offering you, and run with it. Please make this final act of mine worth something by going on to be safe and happy. Because that's all I want for you both now. All I have ever wanted, and unfortunately all I have ever deprived you of. Well, I'm giving it to you now. Dean, Sam, I love you both so much. I am proud to be the father of such amazing young men. Mary would be proud of you both too. You are sons any parents would be honored to have, and and don't forget that. _

_Love,_

_Your Father_

**Secondary Author's Note: Thank you so much for reading! Reviews and suggestions for letters are totally appreciated! :)  
**


	10. Coping Mechanisms

**Author's Note: This one is for m1tchells, who requested a letter from Dean or Sam to John at any point. Well, m1tchells, I chose to write one from Dean to John during Dean's downward spiral late-mid season 7. Dean is writing a letter to John while kind of drunk. (No, John isn't meant to be alive during this. I am sticking to the show's storyline still.) I want to thank jojospn, reannablue, mb64, and flygirl33 for their kind reviews. I also thank everyone who reads/has read these.  
**

**Disclaimer: They're not mine. It's not mine. Heck, I'm not even mine because I belong to Supernatural. lol **

_Dad,_

_ I think I finally understand. Why you did everything you did? Why you yelled and got drunk, and clung to hunting like a lifeline, even though it was anything but. You were scared and angry and sad, and the hunt was what kept you sane. It was the outlet for all the pain you felt inside. I get it now. Because I'm living it now. _

_ I fight with Sammy, and drink like a fish, and I am so obsessed with the pursuit of Dick Roman that I can barely function other than to look up ways to gank the SOB. All it takes is loss to push someone to this point I think. You lost your wife. Lost mom. I lost my friend Cas, and then Bobby, and now I'm terrified that I might be losing Sam too… And that's not all I've lost. That's just the recent stuff. _

_ I used to wonder why you never quit hunting while you were ahead. Before it could become the train wreck that was waiting just around the corner. Now I see you kept going because you weren't sure how to have a life without what had been taken from you...without mom. And hunting distracted you from needing to figure it out. Well Now I'm hunting for the same reasons. Because I don't think I can do it, dad. I don't think I can live without Sammy if he goes. He's getting worse, and it's killing me to watch. _

_ Remember when you said I might have to kill him? Well, I think I did. It just took me a long time, and I didn't intend to do it. I let him go to Hell, dad. And then I got him back, and then I got the real him back, soul and all, and now he's wasting away from some kind of post-hell trauma. And it's on me because I let him jump. For what? To save this freaking world? This world that is literally nothing but pain, loss, and a bunch of stupid people stumbling through it all...  
_

_ So yeah, I finally get why you were the way you were. Because I feel it too much when I'm not hunting. So I keep going and going and hunting and killing. Because when I'm not, I'm feeling and thinking. About Sammy, and Bobby, and Cas, and every other freaking person I've lost or hurt. You said once that when you closed your eyes sober, you would see her on the ceiling, so you liked to close them drunk instead. When I close my eyes I see their faces, each and every one. So I use whiskey to make the faces blurry. So I can't really see them clear enough to feel the pain all over again. _

_ I'm sorry I judged you for your coping mechanisms. Now I understand it all too well. Have I mentioned, you're there too? When I close my eyes. I see you there, and I'm sorry you died because of me. I thought I should let you know, so you don't think I've forgotten. That one was my fault too. I'm gonna stop writing soon, because I'm finally getting drunk enough to have a hard time controlling the pen. Takes me a long time to hit that point now. Longer each time too. I'm scared, because I have no clue what I'll do when I can't drown the pain with alcohol anymore. I'm scared I'll have to face the faces all the time. I guess I'm just plain scared. Anyway, I just wanted to let you know, I no longer hold it all against you. Because I finally understand. _

_Dean_

**Secondary Author's Note: I didn't expect to hit a tenth chapter when I started with the first letter, so thank you all so much for inspiring me to keep going! Reviews and suggestions/requests are much appreciated! **


	11. Broken Oath

**Author's Note: This is the other half to my fulfillment of ClassyMuse's request for letters from John to the boys. Also, A Guest requested a letter from John to Dean, so I am covering that suggestion with this as well. This one is from John to Dean on Dean's eighteenth birthday. Naturally, John never actually gave this letter to Dean. Silly John. :P I want to thank jojospn, ClassyMuse, mb64, knwinchester, reannablue, and m1tchells for their lovely reviews. And thank you again to all you wonderful people who take the time to read these letters!  
**

**Disclaimer: Supernatural doesn't belong to me. Quite the opposite actually... :)  
**

_Dean,_

_ I am writing you this letter to apologize for screwing your life up. Simply put, I messed up big time after your mother died. I went so crazy with grief and rage, and determination to hunt the thing that took her from us…I lost sight of myself along the way. You suffered for it. You and Sammy, but mostly you. I haven't been the father to you that you've needed. I made you grow up fast, and learn how to use weapons, and I put you in harm's way. _

_ Sammy is lucky to have you, because there's no denying you've been a better father figure to him then I could ever be. I am so proud of you, son, for being such a strong young man. For never complaining when I needed you to watch Sam, and for never complaining when I needed you to take care of me. It's unfair that you've had to be so much since you were so young. I should never have asked it of you. Any of it. Not for you to hunt, or to be responsible for Sam, or to travel from crappy motel to even crappier motel, making the best of the crappiest childhood in history. _

_ But I am so amazed at how well you handle it. You truly are an impressive guy. Not many could take what you've been given, and turn it into something good. But you have. You've protected your brother, and me, and kept our little family glued together, even when I seem to be doing my best to tear it apart by risking everything with the constant hunting. _

_ You deserved better Dean, and I should have been the one to give it to you. But I won't say I'm not proud of who you've become. Messed up as your home-life, and education, and everything so far has been, you have turned into an incredible man. For your eighteenth birthday, I was hoping to give you a college fund. That was the plan the day you were born. I went to the bank and opened the account, made the first deposit, and swore to give you the brightest future I could._

_ I broke that oath, but I still want that for you. I might have messed things up, but I want for you to go on in life and have a bright future. I want for you to quit hunting one day, and get married, and have the apple pie life you were robbed of in your youth. When we find the thing that took Mary from us, and we finally end it all, I want you to leave this lifestyle behind you. To be free of it. Because although I don't have the strength to tell you to stop now while you're ahead, even though I should. Even though I know you could die young, and I'm only keeping you in it because I'm selfish and need you by my side when I take the bastard down. I still want for you to be free eventually. _

_ So, though I won't do the right thing and give you that freedom now, I am giving you what little I can. Dean, the impala is yours. At least you can have that much freedom. I know you love her, and you'll be good to her. You'll give her all the care I should've given you. And one day when you have kids of your own, and you're amazing with them like I know you'll be, you can pass this car along to one of them. _

_Love,_

_Your Father_

**Secondary Author's Note: All of you who read these are amazing, and I welcome your reviews and suggestions for letters! :D**


	12. A Simple Apology

**Author's Note: Ok, so this wasn't anybody's suggestion or request. This was one of the letter ideas I've had swirling around in my brain for a while now, and had to do something with. This is a letter from Sam to Dean written mid-season 8, explaining why he went off and had a "normal" life while Dean was in Purgatory. Hope you like it! I also want to thank jojospn, mb64, ClassyMuse, and a Guest for their reviews. And thanks to everyone who reads/has read these!  
**

**Disclaimer: I'm not the owner of all this awesome known as "Supernatural". **

_Dean,_

_ I am writing this because I just can't bring myself to try and explain to you out loud the reasons for my actions. The reasons I didn't tear the world apart trying to find you, and instead adopted a dog and a moved in with a woman. I don't think you'd let me finish talking anyway, and I don't blame you. At least this way you can pick the letter up again later after you've finished with your initial rejection of these words: I'm sorry. _

_ I'm starting with a simple apology. I am sorry for not trying harder, because it's maybe my fault you had to go through an entire year of monsters, and fighting, and constant threat of dying. Maybe if I had tried harder to bring you back, I could've found some way to bust you out sooner. So yeah, I'm sorry._

_ But I want you to understand why it is I didn't. I know you think I just didn't care enough to try. Or maybe you're convinced I preferred the idea of a normal life to the idea of bringing you back. Both of those notions are dead wrong. I won't deny that I don't dream of being a hunter forever, but I would have given anything to have you back. The truth is that I didn't know you were just 'gone', and not 'dead'. I believed you were dead, Dean, and short of pissing you off royally by selling my soul for you, I couldn't think of a damn thing I could do to change that. _

_ It hurt. I mean, the suddenness of it is what really got to me. Even when you went to Hell (which, don't get me wrong, was the worst day of my existence) at least I had a warning. This time…Well I guess I had grown too used to you making it out of impossibly dangerous situations in one piece. And then out of nowhere you vanished, and I was convinced you had died somehow._

_ At first I thought "He'll be back, because he always comes back." But you didn't just pop up, and then something in me broke. I became terrified. Because what if you didn't return? What if this was that one time when it's final? I realized just how miraculous it had been that we both kept bouncing back, and had to see things realistically. How likely was it that would happen again? I couldn't bring myself to keep thinking about you making it back, because it would only hurt that much more if you didn't._

_ So I left that room at Sucracorp and forced myself to drive away. To not go mad with grief. To find a way to live. You had always told me to do that if anything happened to you, and you're right when you say I always disobeyed because I love you. I didn't stop loving you Dean. I stopped trusting there was enough good in the world to make it a possibility that you would come back again. That I could be so lucky as to find a way to magically restore you to health, again. _

_ I had just lost everything again. Cas, Bobby, and then you. I couldn't bear the thought of feeling so hopeful about you coming back to me, and being crushed all over again. I was afraid, and I ran._

_ But I didn't forget you. I didn't even try and push away the memories. When I did live with Amelia, I want you to know she learned a lot about you. Not about the hunting, but I told her other stories, and showed her the few pictures I have of you. I told her about how you raised me, and always protected me, and were my best friend since birth. I told her how much it hurt to lose you. I told her that I had loved you more than anyone in the world, and that when you died I felt like my whole world had died with you. Believe me, she knew you. Because I never forgot about you, and I wanted there to be more people in the world who wouldn't forget about you too. _

_ You want to now the sad, ironic truth? I never gave up that small part of me that hoped you would come back. That little spark that believed maybe, just maybe, the world wasn't as dark as the bigger part of me feared. Guess I should've blown on that spark. Tried to grow it into a fire. I guess I messed up. Like I said before, I'm sorry I was so pessimistic, because if I hadn't been, I might've been able to have you back sooner. But Dean, above all else, I'm just glad to have you back. And don't you ever doubt it. _

_Love,_

_Sam _

**Secondary Author's Note: Thanks for reading! I am definitely still interested in requests/suggestions, and reviews make my day. :)**


	13. The Best Thing

**Author's Note: This is yet another letter idea straight from my own brain. After jojospn had me write the letter from Sam to Dean about Dean's deal, I got to wondering what Dean would have to say Sam about his deal. This was born of my ponderings. lol I want to thank jojospn, m1tchells, a Guest, and reannablue for their reviews, and to thank all of you who've read these for your support!  
**

**Disclaimer: Supernatural is not mine. **

_Sammy, _

_ I want to say I'm sorry. I am sorry you are going through this, and I'm sorry I'm making you go through it as opposed to me. It's the only case in which I would rather you have to be hurting than me. But I couldn't watch you laying there and not do everything in my power to fix it. You were gone, Sammy. I just couldn't deal with that. _

_ And I know I'm being the biggest jerk in the world for making you deal with it. I know it's really screwed up of me to ask you to let me die instead. But I want you to know, sorry as I am that you'll be stuck with that pain, I don't regret it. I would sell my soul for you again in a heartbeat because seeing you up and walking, and bitch-facing, and just plain breathing again… After I had seen you laying there so empty? I knew the moment I saw you standing there that I had made the right choice._

_ I wish it didn't have to be either of us, but that's not how things ever work, right? Not for our family. And so help me if I won't go down with a smile on my face knowing that I saved my family. Because that's what you are Sam. The only thing that remains of my family. And I was supposed to let you go? _

_ Again, I know. I'm asking you to let me go. But you know what? I'm older, so I get to make the call. And I say that as long as there is anything at all that can be done to protect you, I'll do it. I know it's messed up. I hope you know I really am sorry I've put you through so much. I'm sorry I couldn't save you before all of this crap happened. I'm sorry I let you get hurt, and am still letting you get hurt by my selfish actions. _

_ But now I'm going to do an even more selfish and hypocritical thing. I'm demanding of you Sammy: Don't. Sell. Your. Soul. I know you've thought about it. I know you'd do it. Even just to show me that two can play at that game. It isn't a game Sammy, not to me. Keeping you safe has been my job since as far back as I can remember and I do it gladly, because I'd do anything for you gladly. I know you would do anything for me too. And I know you want to protect me too. _

_ Just please don't try and protect me this time. You say you'd do anything for me? Well, what I want from you is for you to go on. Have a life and be alright. If you can do that…If you can live that normal life you've always wanted, then it means my job is done. Because you're not hunting and you're safe and you're happy. Please, Sammy, be happy. Don't you even for a moment feel guilty, blame yourself, or any of that girly emotional crap you do. Just go live your life and remember that's the best thing you could ever do for me. _

_I love you Sammy. Always have, and always will. _

_Dean_

**Secondary Author's Note: Thank you for reading! I want to let reannablue and a Guest know that I have not forgotten their suggestions. I'm working on them! :) And to all the rest of you awesome people, reviews and requests for letter are always great!  
**


	14. More Than You Even Know

**Author's Note: This is for reannablue, who gave me this prompt: "Maybe Sam leaves a letter for his brother (Season 2 after Croatoan when Dean tells Sam about Dad's secret dying declaration/warning) when he takes off in the middle of the night to Indiana." So here it is! A letter from Sam to Dean before Sam sneaks of to investigate the other "special children". Thank you to jojospn, a Guest, another Guest, and ClassyMuse for their most recent reviews. And thanks to all of you great readers!  
**

**Disclaimer: I don't own these wonderful men, or their wonderful-in-a-really-messed-up-way world. **

_Dean,_

_ First off, I want to say I understand why you didn't say anything sooner. What could you possibly say that wouldn't sound just plain terrible? "Hey, so dad said I might need to kill you, because you're probably turning into some kind of dangerous monster. Thought you ought to know." Not exactly the kind of conversation one brother wants to have with the other. _

_ I know I was angry with you before but I'm not now. I'm angry at dad though. Shouldn't he have been the one to warn me? Shouldn't he have told me I might go dark-side and try killing people or something? I know he'd say he was just protecting me. But that's not true. That's what you're doing Dean. What you've always done. Dad didn't tell me because he was protecting himself. He didn't want to have to admit that he had even considered putting his own son down. _

_ But, Dean, I'm so grateful you did tell me. And I want you to know that if you do have to take me out, I'll be glad to let you. If I'm not completely crazy. If I am crazy, don't listen to me when I tell you not to shoot. That isn't the me I would want to be, and whatever potentially-evil Sam says, he's wrong. I would want you to do it. To end me before I can end a bunch of innocent lives. Don't hesitate, Dean, because the real me wouldn't thank you if I killed a bunch of people because you couldn't pull the trigger on me. _

_ God this is so messed up! Here I am begging my brother to definitely kill me, but only if necessary. You know, necessary...like if I suddenly turn into a monster. What exactly is supposed to happen to me anyway? Am I going to sprout horns? Are my eyes going to turn yellow? I swear, Dean, if my eyes go yellow you better shoot me on site. _

_I'm scared, man. I don't know what to do. How am I supposed to fight something that's hiding somewhere within me? I wish you didn't have to bear this burden. Knowing you might have to kill me, I know it's really messing you up inside. But if it means anything, I want you to know I'm truly grateful to have you with me in this. Much as it hurts me to see you hurting because of me, I don't have a clue what I'd do without you. _

_ You're the shoulder I can lean on every time I start to panic. Because I know that no matter what happens to me you'll help me through it and you'll be there for me. And if I do go dark-side…If I have to be put down...Well, I know that afterwards you'll remember me for who I really was. Or at least you'll remember me as Sammy the chubby twelve year old. But it's better than being remembered as a freak. So thank you Dean. Thanks for telling me, and staying with me, and being my source of strength more than you even know. _

_But now I've come to the harder part of this letter, because it's going to tick you off. I know you want us to lay low and to wait until this all blows over, or at least until we understand it better. But Dean, I can't just sit on my thumbs while something dark is happening inside me. Face it, we won't get any information by laying low and you know it. You're saying we should go to ground because you want me safe. Like I said, I'm really grateful you've chosen to stick with me in this and that you have my back. But I need answers Dean, so I'm off to find some. I'm going to go look into the other "special" kids. If I can learn more about them, then maybe I can learn how to fix whatever this thing is that's supposed to be happening to me.  
_

_That's it, I guess. You can commence with the whole "being pissed" thing. But please don't forget, I'm not running away from you and I'm not angry. I'm just not willing to be idle. Hopefully I can find some answers that will help. Hopefully you'll never have to kill me, and one day we'll look back on this and laugh at how screwed up our 20's were... Hopefully you'll understand. _

_Sam_

**Secondary Author's note: Thanks for reading! I've got a growing lists of requests here, and I love it! Feel free to send me more. :) And as usual, reviews are very much appreciated! **


	15. Comforting

**Author's Note: So a Guest left a review saying they "would love a letter from Dean to Mary", and this is what came of my attempt to write one. Hope you like it! Thank you to jojospn, m1tchells, and reannablue for their most recent reviews, and thank you to all of you awesome readers!  
**

**Disclaimer: I don't own _Supernatural_. If I did it wouldn't have lasted this long, because I'm no where near as good a story-teller as the amazing Mr. Kripke. :) **

_Mom,_

_ We did it. We took down the demon! Yellow-eyes. Azazel. The dick who took you from us. Sammy and I ganked him, and even dad managed to be there to help. Leave it to dad to find a way to bust outta Hell just in time to finish the job… It's inspiring. Maybe I'll be that lucky too, huh? I'm sorry, I don't mean to make this a depressing letter. But I can't think of anyone else I could tell how I'm feeling about the situation I'm in. _

_ I'm going to Hell in a year mom. I sold my soul to save Sammy's life, because some dick-bag minion of Azazel's stabbed him in the back, and he was dead, and I had to fix that. So I made a deal with a demon. Sammy's life for my soul. Don't get me wrong, I definitely don't regret it. Sammy is safe and that will always mean more to me than anything… But to be honest mom, I'm terrified. _

_ I can't tell Sam because I have to stay strong for him and pretend like it doesn't bother me. Otherwise he'll just feel upset and blame himself, and I don't want to hurt him anymore than I already have. The poor kid's been through enough and I just want him to be ok, you know? That's why I did this in the first place. To protect him. It's what I've always done, and what I'll keep doing until those freaking hounds come and drag me away. .._

_ But I don't actually want to go to Hell. It sounds stupid even saying it. Because really, who does want that? But I mean I really don't. I never tell Sammy, but I want a normal life just as much as he does. Maybe even more than him. I want a wife, and two point five kids, and a minivan. Ok, well I don't actually want the minivan, but you know what I mean. I want to have a family and a future. I want to be happy. _

_ I don't want to waste away in some fiery pit. And I mean just thinking about the pit makes me nervous. I consider myself to be pretty tough. I've taken punches, stab wounds, even a bullet or two… But I don't think I'm tough enough to last in Hell. Quite frankly, I'm sure I'm not. But that's life, right? It's never easy. Of course it was never just going to be a straight forward, cake-walk, "kill the demon, live happily ever after" thing. _

_ Something had to go wrong, because something always goes wrong. That's why you got killed, and why dad wound up dead, and why Sammy ended up lying there on that freaking mattress all quiet and still…And of course I was going to sell my soul for him. Because nothing, not even an eternity in Hell, can dissuade me from saving my little brother. So I guess I'm ok with the decision I made. I guess I'm even proud of it. Overall mom, I guess I'm really just scared. _

_ I wish you were here to tell me everything would be alright. To tell me angels are watching over me and to make me believe it. Because, ironic as it is with where I'm going, I want to believe that now more than ever. That maybe there are angels out there who care, and a chance that I can be saved from it all. It's unlikely, but what kind of son would I be if I didn't trust my mother? So here goes mom. I'm trusting there's an angel out there somewhere, watching over me, who cares enough to save me from this mess I'm in. _

_ Oddly enough I find it comforting to say that. Even though it's ridiculous, it makes me feel like I'm close to you again. So thanks mom, for being there for me even now. _

_Love,_

_Dean_

**Secondary Author's Note: Thank you for taking the time to read my fifteenth letter! Your reviews are always appreciated, and requests/suggestions are always welcomed. :) **


	16. The Light I See

**Author's Note: This is not based on any suggestions, but it just sort of happened when I went to write something totally different, so I figured I would publish it. This is a letter from Sam to Dean taking place shortly after "Pacman Fever", but before they learned what the third trial will be. I want to thank reannablue, a Guest, jojospn, another Guest, and mb64 for their incredible reviews and support. And as usual, thank you so much to all you fantastic readers of these letters. Chuck bless you all!  
**

**Disclaimer: I am not the person who own****s**_** Supernatural.** _

_Dean, _

_ First, I want to clarify that this letter isn't about me giving up, and it isn't a "let's say our goodbyes now just in case we can't later" thing. I know you thought that the moment you saw I'd actually written you a letter… I swear I want to keep fighting as long as I can. I'm not quitting these trials or giving in to them. I just want to say some things, so here goes…_

_ I feel like crap, Dean. These trials are really kicking my butt. Sometimes I just want to crawl into bed and never get up again, and other days I just want to run full force at the third trial, just to end it already. I'm tired, shaky, and I hate the fact that I can't even fire my own gun. Basically, I feel like death._

_ But I don't want to die, Dean, I promise. That's why I took these trials on. Because I know that I see a light at the end of this tunnel, and it isn't Heaven's shining gate or the fiery pit of Hell. It's a wife, and maybe going back to school, and having a couple kids that I know you'll spoil rotten. I know that I believe it can end well, and therefore I've got to be the one to do this. Because honestly you were scaring me with how readily you'd throw yourself at a job like this. With how much you seemed to want to die. _

_ And so I did the only thing I could think of to force you to keep going... I put myself in danger. See, I know you well enough to know you wouldn't let go if I needed you. And I definitely need you, man. I need you there fussing over me, even when I tell you to stop. I need you there to force me to take breaks when I am trying as hard as I can to work myself to death. I need you to crack lame dirty jokes that make me laugh out loud when I don't even want to smile. I need you to be there to remind me of why it is I did this. And you do remind me, just by being around.  
_

_ I accepted these trials not just because I wanted to stop you from getting yourself killed. I mean, I definitely stick by that as reason number one… But I also took them on because I wanted to give you the chance to really live. Dean, if we close the gates of Hell forever, then you can finally have a life too. I remember that you used to want one. A life, and family, and a real home? Yeah, a whole mountain of crap happened and your perspective changed a bit. But I believe that somewhere inside of you that desire still exists. And I'm going to do everything in my power to help you get that life you wanted. The life I know that deep deep down, you still want. _

_ Because these trials are dangerous, and hard, and I knew that going in. But you know what? As long as I have faith that things can get better, and more importantly, as long as you're there to back me up and remind me what "better" even is, I think this closing the gates of Hell thing can be done. And I'm going to do it.  
_

_ Sam_

**Secondary Author's Note: I promise I am still working on the list of requests I have for these, and thank you all so much for your continued interest and support! Reviews and even more requests are totally awesome. :)  
**


	17. Eternity

**Author's Note: So this one is for ClassyMuse, who requested a letter from Dean to Sam regarding Dean's own time in Hell. I admit this was probably harder for me to write than any of my other letters, so I hope it turned out half-decent. lol It is a letter from Dean to Sam, set shortly after Dean tells Sam about Hell during that scene by the Impala. Thank you to m1tchells, mb64, a Guest, flygirl33, and reannablue for their most recent reviews. You guys rock. :D And thanks to everyone who reads these! (You guys also rock. 3)**

**Disclaimer (in 5/7/5 Haiku form): **

**Of these characters, **

**not a single one is mine. **

**It makes me feel sad. ****;) ****  
**

_Sam,_

_ So I guess I don't have it in me to talk to you again about Hell. I know you just want to help, but man, there are some things I just can't handle speaking about. But I have to let it out somehow. I know I do, because if I don't it'll definitely kill me. And then I'm certain that I'll be right back in Hell. So this is a letter about the stuff I can't even say. The stuff I don't want to say, but I know that I have to say. _

_ First of all, whatever you're imagining about what Hell is? It's worse. If you think it's hot, I can tell you it's hotter. If you think it's dark and creepy, I can tell you it's pitch black and freaking terrifying. It's an endless wasteland of blood and suffering. I spent thirty years in that wasteland as a victim. I spent my days subjected to Alastair's creative torture. I spent my nights hanging from chains that bit into me and wondering if I could somehow kill myself in Hell and escape. _

_ Not that Alastair hadn't offered me another way to escape. "Torture another soul, and be free of the torture yourself." That was the offer I got every day before the pain began. And each damn time I told that white-eyed bastard to piss off. It hurt, and I hurt, and I wanted nothing more than to be free of the pain. But not like that. Never like that._

_ But days turned into weeks, which turned into months and years. Decades eventually. And I guess eventually I stopped caring. I felt like there was nothing left to care about. Eternity really seems a lot longer once you've experienced thirty years of it. So I guess then something in me broke. I thought about how there really was no end in sight. About how I could suffer forever and about how there was no point. Nothing I was fighting for. There was nothing at all. And so the next time that dick made me his offer, I cracked and I…well you know what I did. _

_ I am not justifying my actions at all. I guess I'm just trying to understand them. I think what did it for me was my knowing there was nothing left for me to be strong for. I've always fought hard because someone needed me to. The monster's victim needed me, a friend needed me, and most importantly Sammy, you needed me. But down there no one needed me. Even the soul they offered me didn't, because if it wasn't me, it'd still be someone else hurting them. There wasn't a point. _

_ Now I realize there was a point. They were offering that escape from pain to me because they needed me to do what I did. I wish I'd known. If I had even the slightest inkling of what their plan was, I'd have let them rip at me for all of time, because I would have been doing it for something. So the first seal stayed sealed. So the innocents on Earth remained safe. So that _you_ would be safe.  
_

_ I bet you understand now why it is I don't talk about this stuff. I will never, as long as I'm alive, be able to forgive or forget my actions. But I am grateful that you have tried to forgive them. I want you to know that in the forty years I spent down there, not a day went by that I didn't miss you. My pain in the ass little brother who I failed, and yet he still sticks by me. __I don't deserve to have such a supportive brother, and I appreciate it more than you know._ So thank you.  


_ Dean_

**Secondary Author's Note: This was definitely darker than the other ones, so sorry if I made anyone feel sad. I've got more requests I'm working on, and feel free to keep 'em coming! Reviews are also very much appreciated. :)**


	18. To Keep In Touch

**Author's Note: This is for reannablue, who left me a review saying "_I was thinking that maybe Sam wrote John a letter ... asking to go home or asking John to reconsider cutting him out." _This is my attempt to fulfill that request. :) My thanks go out to jojospn, mb64, a Guest, and Garideth for their recent reviews and support. I am also grateful for all of you amazing readers!  
**

**Disclaimer: I don't own_ Supernatural_. **

_Dad,_

_ I guess I'm writing you this letter to say sorry. I'm not sorry I left, because I stand by my decision to pursue the life I want to live. I'm not sorry I kept my admission to Stanford a secret for so long, because if I hadn't, I know I you would have found a way to get me to stay away from the school. But I am sorry for all those things I screamed at you. I said that I blamed you for my unhappiness, and that you had done a crappy job raising Dean and I, and that I hated you. None of that is really true._

_ I blame the thing that killed mom for my unhappiness, because it was the push that got the ball rolling. If it wasn't for that thing, life would have been so different. Not just for me, but for all of us. Dean would have been a regular old teenage rebel. I would have been a typical scholastic nerd. You and mom would've had a life, and jobs, and been proud of your sons for all of the normal things they did. You would've celebrated Dean's high school graduation, instead of skipping it to take down a shifter. You would've been proud of my admittance into a good college, instead of being pissed that it meant you were losing a hunting partner. I was unhappy, dad, because I have always wanted normalcy. You didn't ruin that for me. That creature did. So like I said, I was wrong when I blamed you. _

_ I also said you had failed at raising Dean and I. That's not true either. You raised us well and have always done the best you could with what cards you were dealt. You taught us how to be strong and how to take care of ourselves. True, it's pretty messed up that you were giving children firearms to sleep with at night…But I know why you did it. You caught a glimpse of the real darkness in the world and chose to protect your sons from it in a more legitimate manner than hiding it all from them. Than just telling them that everything would be fine. You didn't pretend the world was safe. Although there were plenty of nights I wanted nothing more than for you to tell me that everything would be fine and Dean and I would always be safe, I understand that you were protecting us by being honest. You forced us to be stronger than most kids, but in that sense, you also raised us to be very capable people. You raised us well. _

_ Finally, I told you I hated you. Of all the things I shouted, that probably hurt you the most. I'm so sorry dad. I don't hate you. You and Dean are all I've had my whole life, and you are both everything to me. I was wrong to say something like that without thinking first. I was caught up in the heat of the moment with anger, and frustration, and even a bit of fear. I let those words slip out before I could stop them. It was wrong, and it certainly wasn't true. You're my dad, and I love you. _

_ I guess that's it really. I just want you to know that I might have gone off to college, but I don't want that to mean I'm gone from your life forever. I know you think that's what my leaving meant. But you and Dean are my family. I know we aren't a normal family. I know we are about as damaged as they come…But I still want to be one of you. So if you're alright with it, I'd really like to keep in touch. _

_Sam_

**Secondary Author's Note: Thanks for reading! I am still working on requests, and am always open to receiving more. Reviews are also totally great, so feel free to leave a comment! :)  
**


	19. Ok Guys

**Author's Note: This is a letter "from Charlie to both boys", as requested by mb64. :) I want to thank reannablue, mb64, and Garideth for their most recent reviews. I also want to thank all of you great readers who continue to support me as I apparently document the whole series in letter form. lol **

**Disclaimer: I'm not the one who owns _Supernatural_. **

_Ok Guys,_

_ So first I want to thank you both. Not just for saving my bacon, but for helping me do the right thing for my mother. I guess you both understand about losing mothers, so thank you for helping me through this. But I also want to return the favor, and help you guys through what you're dealing with too. After all, I owe you for being there for me. I know you guys are on a major quest here, and things are getting hairy. I just want to tell you, I believe in both of you and I know you can do this. To put it in perspective, I'm going to use an analogy:_

_ Sam, you're like Frodo in the Lord of the Rings. Only much, MUCH taller. Seriously, you're like twelve Frodos stacked on top of each other… Anyway, you have this quest that you've undertaken, and it is kicking the crap out of you. But you know what? You are going to finish this. Because you're stronger than anyone gives you credit for. I read about when you took down Lucifer and stopped the apocalypse. You didn't give up then, and I know you won't give up now. You are a massively dedicated and determined dude, and you will find a way to finish this. And it helps that you've got a Sam by your side._

_ Dean, you're Sam. (I shouldn't have to, but I will still clarify: Samwise Gamgee, not your brother.) You're the guy that will do anything for your friend, even if it means walking to the ends of Mordor and carrying him the last hundred feet up the mountain. You have given everything for Sam. (I do mean your brother this time.) You have protected him, and been loyal to him, and continue to take care of him. And it makes all the difference in the world. Sam needs you there for him, and he'll get through this because you're there to help. If he falters, you'll be there to get him back on track. You were there in that cemetery when it looked like Sam was gone forever, and I know that's what gave him the strength he needed to finish the job. If needed, I know you'll be there to lend him that strength again. _

_ You are both awesome men, and if anyone can handle slamming shut Hell's gates, it's you two. I've never met guys who fit the hero bill better than you both, and I am honored to say I know you. Sure, knowing you has gotten me into some serious crap before, but it's worth it. Not just because you're cool guys, but because come on… At the end of this, I get to say I know the boys who conquered Hell! Pretty epic. _

_ And I want you to know that, although the rest of the world is oblivious to all the good you've done for it…I'm not. To quote the amazing J.K. Rowling, "No story lives unless someone wants to listen." I want to listen, and I promise I will never forget. __So thanks again for helping me. And thanks again for helping the world, again. You're great, and I know you'll continue to be great. _

_Much Love,_

_Charlie _

_P.S. __Maybe when this is all over, you'll let me write the books for it? I'm just throwing the idea out there… _

**Secondary Author's Note: The fact that you just read this letter makes me smile, so thank you! Reviews are much appreciated, and requests are very welcome.**


	20. Remorse

**Author's Note: Alright. So this is letter number twenty, which I hadn't even _imagined_ reaching when I started this whole series... Thanks to a guest named "WomanOfLetters", I realized I hadn't done any letters involving Castiel yet. So in celebration of my twentieth letter, I decided to really challenge myself. This is an apology letter from Castiel to Dean, written sometime shortly after 8X17, "Goodbye Stranger". Of course Cas is bad with the whole "postal service" thing, so this letter never actually reached Dean... :P Like I said early on in this series, I am not writing slash fiction and I am keeping it as cannon as I can. So this letter is not a slash letter. (Unless you are a Destiel shipper and choose to view it that way. I don't discriminate, but I personally wasn't aiming for that when I wrote this.) Thank you to OlegnAiDociN, mb64, the guest WomanOfLetters, jojospn, and flygirl33 for their recent reviews. You guys helped me hit 100 reviews today! So much joy, I don't even know how to express it in words. 3 And infinite thank-yous to all of you spectacular readers who have supported me this far. I couldn't have made it to twenty without all of you, and I am so very truly grateful! :D **

**Disclaimer: I don't own Supernatural.**

_Dean,_

_ I am writing you a letter because I believe that appearing suddenly in your room or vehicle would be an inadvisable course of action considering recent events. The purpose of this letter is to attempt to explain and repent for said events. It was never my intent to harm you Dean. I suppose it could be said that as a result of Naomi's manipulations, my intent in that moment was in fact to bring you harm. However, as myself, I would never seek to hurt you. _

_ She was in my head, Dean, telling me what to do. She was telling my vessel how to move. She trained it, my vessel. She had me practice a thousand times, attacking and murdering a fake you. This training, combined with some sort of mind alteration which I can only vaguely remember happening, resulted in her ability to separate my body and mind. I was present, but she could put my vessel "on autopilot", as you would say, and remove my mind from the situation. She could force me to do things, and I was essentially helpless to prevent them. _

_ I want you to know I am aware that you have no reason to trust what I am saying, or to believe in me. Not as you once did. Once, years ago, you said I was like a brother to you. I rejected your sentiments at the time because I was foolish. I see now how much that offer was really worth. I should have seen then, considering I had observed the lengths to which you would go for Sam, your true brother. But instead, I committed myself to a failing course of action, shunned you, and all but destroyed our friendship. _

_ Now I see the error in my judgment. I should have thanked you for the offering of such a sense of family, and the unwavering loyalty that came with it. I should have stopped while I was ahead, and listened to your advice because you were only trying to do what any good brother would. You were only trying to save me from myself, as you had done for Sam so many times before. I rejected you then, and I regret it now. _

_ I see clearly how much suffering has resulted from my mistakes. If not for my actions, so many people and angels would still be alive. So many innocent souls would never have been claimed by death. The tablets would not have been unearthed, and Naomi would have no reason to seek control over me. She would have no reason to want to end your life. But the thing that would have changed, and the change that would have mattered most, would be you Dean. _

_ You would never have suffered through Sam's internal wall collapsing. I take responsibility for that fully, and express my deepest sorrow for having made the choice to do that to him. You would not have lost Bobby, whose death is, albeit indirectly, certainly related to my mistakes. You would not have gone to Purgatory, and therefore would not have spent one miserable year living as "monster bait" as you once said. You would perhaps have lived a normal life with that woman and her son. I also take responsibility for ruining that for you, and regret it every day. I made these mistakes originally because I sought to protect you from yet another battle. In the end I brought the war to your home and you have every right to hate me for it._

_ Perhaps the saddest thing is that I know you don't. Although I know you have no reason to put any faith in me or to care about the tattered remains of our friendship at all, I know you do care. In Purgatory, even when it seemed apparent that I must have abandoned you again, you fought endlessly to reach me. And you blamed yourself for my choice to stay in that realm, even convincing yourself I hated you because of it. And just recently in that crypt, you called me family once more. Offered me that link to the brotherly connection I thought I had brutally severed long ago. You have made it clear that you are a true friend to me. You have shown me that you are family unlike any angel I have known. _

_ And so I apologize, wholeheartedly, for having left you in that room confused and abandoned yet again. Only this time I swear to you on my grace that I did not leave because I believe I am better off alone, or because I have some dastardly plan for power that will result only in more pain for you. I left because I had to. This tablet…It is my core objective to keep it safe. I must keep the tablet safe and separate from all who could threaten it. I don't personally see you as a threat, but there is no denying that you 'fit the bill', so to speak. If I were able, I would be there to help you protect Sam, to beg your forgiveness in person, and to thank you for once again not giving up on me. For once again showing me that you are a brother to me, even when I am far from deserving of your kindness and devotion. _

_ Dean, I meant it when I apologized in that crypt. I know the words "I'm so sorry" seem insignificant, but I cannot think of a more truthful way to express my feelings. I am so full of remorse for all I have done to you and yours. Please be safe while I am gone, and know that when this all has ended, I will return to you. My closest friend. My brother. _

_Cas_

**Secondary Author's Note: To demonstrate my immense gratitude for all of your support, I prepared you a cyber feast. Go ahead and dig in! I even remembered the pie. ;) Thank you so much, and please feel free to keep the reviews and requests coming! :D **


	21. The Least I Can Do

**Author's Note: This is for the wonderful mb64, who requested a letter from Dean to Benny. The letter was written by Dean shortly after 8X19, "Taxi Driver". I want to thank mb64, jojospn, judyann, the guest WomanOfLetters, m1tchells, ClassyMuse, and olegnAiDociN. for their recent reviews and support. And thanks again to all of you incredible readers!  
**

**Disclaimer: _Supernatural_ is not mine. :P **

_Benny,_

_ First off I want to thank you. I don't even know how to begin to thank you, and it seems pretty douchey of me to even try seeing as I've really let you down…But I need to. I mean, you saved my little brother. The one who hated you. Who I chose over you. The one who means the world to me, and would be trapped in Purgatory right now without your help. I don't know how I could ever repay what you've done for him, or repay what you've done for me. In fact I know that I can never repay you. But I'm at least still going to thank you.  
_

_ But thanks aren't all I need to give you. I also need to apologize. I cut you off so quickly and I didn't even offer you a good reason. I just kind of let you go. It wasn't fair, and after everything you'd done for me you deserved a better goodbye than just, "Yeah. It's the end of the line." And then you came back when I needed you, and you gave me everything you possibly could... And I never did give you a better goodbye. _

_ I guess I didn't want to admit it was goodbye. I could tell you probably weren't planning on retuning. I'd have needed to be blind not to see it. But I didn't want to accept it. I wanted so badly to believe that you'd come back and that I'd get to make it all up to you. That I'd be able to finally help you deal with the whole "being a vegetarian vampire" thing, and that you might even come with Sam and me back to our place. I wanted to believe that I could fix my mistake. _

_ And I wanted Sam to see you for what you are. For him to see the loyal friend you've been to me. The sad thing is that he did see it, he just saw it too late. He let me know that he finally understands why I trusted you in Purgatory, and why I continued to trust you after the fact. He trusts you now too I'm pretty sure. _

_ But_ _you're not around to be trusted. You stayed behind in that godforsaken wasteland, and I'm sorry Benny, I really am. Because I should've been the one that gave you a reason to believe you belonged here, and had your back through this whole mess like you've had mine. I should've been the brother to you that you always referred to me as. But I've never ended up being the friend my friends deserve...  
_

_ I guess I should've warned you when we first met, I let everyone down. Remember Cas? I didn't pay attention to him either when he needed my help, and he nearly destroyed himself and the rest of the friggin' world because of it. And Sam? He's been through whole mountains of crap because of me. He's been hurt because of me, died because of me… He's even been to Hell because of me. Speaking of which, he's only trying to close up Hell right now because I wasn't able to do it for him. So yeah, I'm sorry I didn't give you a proper disclaimer, because it could've saved you a lot of trouble. _

_I guess I'm just sorry in general...  
_

_ I refused to burn your remains. I know it's a bit late to be thinking like this, but I miss you and I'm not letting go. Especially not after what you've just done for us. If I find the tiniest possibility of a way to bring your ass back here, you better believe I'm going to do it. __Until then, the least I can do is say thank you. I just wish I could say it to your face. __So here's to the painfully optimistic hope that I'll find a way to see your mug around here again. _Because I might have messed up and failed you, but I'm not going to use that as an excuse not to care anymore. I care, and I'm grateful, and I'm so freaking sorry.  


_ Dean_

**Secondary Author's Note: Thanks for reading! Feel free to review and/or throw a suggestion at me. I love them. :)  
**


	22. Mother's Day

**Author's Note: This letter is for judyann, who requested** "**A**** young Sam (teenager) writing Dean a thank you letter for being like a mom to him. Maybe for Mother's day." In this letter I am going to say Sam is about 14. I want to thank mb64, jojospn, flygirl33, the guest WomanOfLetters, and knwinchester for their awesome reviews. And thanks to everyone who reads these! **

**Disclaimer: I don't own _Supernatural_. **

_Dean,_

_ So in school today I was given a pretty screwed up writing assignment. I was given one hour to write a short essay on what my family is doing for mother's day. I thought it was messed up for so many reasons. First, does the school not care that not every student has a mother, and that a prompt like that will only remind us mother-less kids about how much it stinks? Second, I couldn't be honest at all, because if I were to tell the truth they'd lock dad up for being a danger to his children. Let's face it, we know that for mother's day we'll either be hunting something nasty, or watching dad drink himself into a coma…But it did get me thinking about mothers, and what they do, and all that stuff. And I came to an interesting realization. _

_You've been my mother my whole life Dean. No, I'm not trying to call you a girl. I just meant that you've taken care of me and done all the mother stuff since I was a baby.I mean, when I was learning how to walk, it was you that was standing at the end of the room with your arms out telling me I could make it. And when I was four and went through my "scared of the dark" phase, I remember you used to make sure I had a night light plugged in next to my bed in every motel, even though it annoyed dad and the glow made it hard for you both to sleep… _

_ And my sixth grade graduation. The one dad wanted me to skip because I'd only been at the school for about two weeks, and I wasn't even going to be in the same town a week later? I remember you convinced him to let me go. And you were there with one of those flimsy disposable cameras, cheering yourself hoarse when my name got called to walk. I was proud of myself for the fact that I was leaving elementary school, but it meant the world to me that you were there and proud of me too. _

_ Oh, and the first time I got stitches! I was like, seven, and I fell over and busted open my knee… You were so fussy! You seemed more scared to give me the stitches than I was to get them. You took forever doing them, because you were determined to make them even and neat, and as painless as possible. And when it was over you told me what a tough kid I was and walked me down the street to get ice-cream. And now whenever I need stitches I don't mind them at all. I just get a craving for ice-cream…_

_ Anyway, I guess I'm just trying to say that you've always been there for me, and since they don't have a "big brother's day", I figured mother's day would work. After all, mother's day is supposed to be about showing that you appreciate everything your mother has done to take care of you. Well you aren't mom, but you're certainly the person who has taken care of me, and I think I should show you my appreciation. So this Sunday I'm going to do something nice for you. And no, I'm not going to make you a card out of macaroni, or a paper flower, or something froofy like that… I just want to do something to acknowledge everything you've done for me. And I'm sure mom would agree you deserve it. _

_Sam_

**Secondary Author's Note: Thank you for reading! Reviews, requests, and free pies are always appreciated! :D  
**


	23. The Awesome Memories

**Author's Note: This letter is for mb64, who suggested a response from Dean to Sam regarding the most recent letter "Mother's Day". Thank you so much to jojospn, ClassyMuse, mb64, reannablue, a Guest, and the guest named WomanOfLetters for their amazing reviews! And thanks again to all of you awesome readers! :D  
**

**Disclaimer: I don't own _Supernatural_. **

_Sammy,_

_ So first off, thanks kid. I have hated every mother's day since mom died, and yet this year you managed to make me enjoy myself. Seriously, when did you find time to bake me a freaking apple pie? And where did you get the supplies and oven for that matter? I'm going to guess you used your puppy-dog eyes to get the motel manager woman to lend you her kitchen for a while, huh? The infamous Sammy eyes. If I can't beat them, she sure didn't stand a chance! _

_ But I want to say more than just thanks for the pie. I mean, it was amazing and all, but I wanted to thank you for the letter too. It never really occurred to me that you think about everything I do for you. And I'm not trying to make you feel bad when I say that, I swear. I mean it never even occurred to me to realize all the stuff I do! But seeing it written down on paper makes me smile. I feel like such a girl saying it, but I got pretty happy remembering all those times you wrote about. _

_ Like when you learned to walk, you know, I remember it perfectly. You kept getting up on two feet and you would get so excited about just that, you would start to kind of bounce around. And then of course you'd fall over from bouncing. And every time you fell you looked like the world had just done you some massive injustice. Finally you got this look of pure determination on your face, and hauled yourself up onto two legs, and the bouncing was gone. You just took a step, and then another… And the bouncing almost started again, but you were fighting it. Your face was fixed in such concentration, like you didn't want to get excited until you were sure of yourself. I stood at the end of the hall and I told you to keep going. And you did. You must be the first kid in history to go from stumbling to striding in no time at all. And when you reached me, you started bouncing like crazy, and I had to hold onto your arms so you wouldn't fall over again and ruin your moment. And I just remember being so proud of you. _

_ As for that period of time when you needed a nightlight…Well it was only fair you got to use one. When I was four and got freaked out by anything, mom would come in and sing me back to sleep. She would come into my room and act like it didn't bother her at all that I'd just totally interrupted her eight hours. And then she'd sing "Hey Jude" and I'd be fast asleep by the time she hit the third verse. So yeah, the least I could give you was a little light…_

_ And that graduation you were going on about? You know, I still have that camera somewhere. I never got around to developing the pictures. I should do that, because I know there's this one shot I got where you were standing on stage holding that sixth grade diploma slip they'd handed you, and you were beaming like a kid in a candy shop. I snapped the picture because I wanted to remember that look you were wearing. It isn't often I get to see you so ridiculously happy. _

_ And you were picking on me for being nervous about giving you stitches, but you don't know how nerve racking that really was! I mean, here's my little brother in pain from a bloodied knee, right? And he needs me to fix him up, but in order to do it I need to hurt him more by sewing that damn thing shut. I have never been so careful with stitches in my life. All I could think the whole time was, "If I mess this up, the kid is never going to trust me again." I guess I'm relieved to hear that experience is such a good memory for you. _

_ So anyway, thank you. You made me remember all the good times. Some of them I didn't even know were good until you put them into perspective for me. It meant a lot, and I might not hate mother's day so much anymore. After all, how can I hate it when you put so much effort into helping me through it? So thank you Sammy. For the pie, and for all the awesome memories. I wouldn't trade them for the world. _

_Dean _

**Secondary Author's Note: Thanks a bunch for reading! Reviews and requests are simply magical. lol  
**


	24. Forgive Me Father

**Author's Note: This letter was not requested by anyone, but I have been contemplating it since the season eight finale. With that being said, this could be considered a spoiler for season eight's finale episode, so please don't read it if you haven't seen 8X23 "Sacrifice" yet... **

**Anyway, this is a letter based off of Sam's confession. In my head, he wrote down what he was going to say because he was afraid of messing it up. And as he wrote this kind of just happened. Anyway, a thank you is in order for jojospn, olegnAiDociN, mb64, and flygirl33 for your most recent wonderful reviews! And thanks to all of you lovely readers. :D  
**

**Disclaimer: I don't own _Supernatural_. But after "Sacrifice", it re-staked it's already existing claim on my soul. lol **

_Heavenly Father,_

_ I don't know if you're listening. Even if you are listening, I don't know if I'm someone you want to listen to. But I've got to do a confession here and I don't really have any priests to talk to. I figure the priests always say that you're listening, so here goes…_

_ Forgive me father, for I have sinned. A lot. So much that I felt the need to write this all down so I didn't mess up my confession, because I seem to mess everything up. I don't even know where to begin, so I guess I'll go back to the earliest part I know I am responsible for._

_ I'm sorry for trusting Ruby. I was so desperate for revenge that I let a demon into my life. I let her teach me how to use the darkness in me, and I wanted so badly to believe I was doing the right thing. But I wasn't, and deep down I knew that. I knew that drinking demon blood wasn't good because it was what started my whole family's mess. Deep down I just liked feeling stronger. Capable. Powerful. So I let that monster keep twisting me and manipulating me, and getting me to do more and more sketchy things. Until I finally let her convince me to kill and innocent woman, drain her, and start the apocalypse. Of course she didn't tell me it would set Lucifer free, but I should have seen it coming. I should have listened to Dean right from the start. Instead I ignored his advice. I abandoned him for a demon, and acted as though nothing he'd ever done for me meant anything at all. Which isn't true, because it means everything to me. _

_ And after all of that, after you saved us and put us on that plane. You cleaned me up, and what did I do? I wandered right into Famine's clutches, and got myself pumped up on demon blood again. Because I wasn't strong enough to resist… Even after you fixed me up, I went right back into that pattern. And my poor brother had to lock me up and hear me screaming again. And the worst part of that was my knowing he cared. He wasn't pissed, but just plain brokenhearted to see me crumble again. _

_ And then there was all the stuff I did when I had no soul. I know technically none of that was my fault. But really, the kind of man I became without my soul doesn't just spring up from nothing. That's got to be the pure essence of the dark part of me that lets me make bad decisions, like when I joined Ruby. So I'm so sorry, because I know I caused a lot of pain. I know I killed innocent people. I know that I let my own brother get turned into a vampire as a means to an end. And I regret that so much. I think now about how it should've killed me to see him like that. To know I might have to hunt him. But instead I actively let him get turned, and I'm so sorry God. _

_ And then there's recently, when Dean got stuck in Purgatory. I didn't even try to find him. My own brother, who sold his soul for me, and I didn't even try and find him when he vanished. I could say it's because I was scared of being let down, or that I genuinely thought he'd died. But even though those reasons are true, it doesn't change how wrong it was of me to let him go like that. After all he's done for me, I just accepted his 'death' and moved on. When he needed me to at least try and come to his rescue, like he's always done for me, I essentially abandoned him. _

_God, it seems like that's all I do! Just looking at this paper I can see it so clearly. I just let my brother down time and time again…I'm so sorry. _

_I couldn't be sorrier, and yet how many times have I apologized to him only to screw up again? What does it even matter anymore when I apologize to him. The words "I'm sorry" are worthless coming from me now. Used too many times, and devalued beyond belief... _

_But I am. I'm so incredibly sorry. _

_ So God, I guess if there's one confession I could make to sum them all up, and to cover my biggest, darkest sin, it would be this: I'm sorry for having failed my brother. I'm sorry for letting Dean down so many times. I'm sorry I have never been the brother he deserves. And I'm sorry that he's always been the brother I don't deserve. The brother who loves me and protects me, even when I betray and hurt him. Even when I abandon him. Even when I sin. I'm sorry, God._

_I'm sorry Dean. _

**Secondary Author's Note: Thanks for reading! Feel free to review, and remember that requests are always welcome! **


	25. Newsflash

**Author's Note: So this letter is for Leia 96, who requested a possible letter from John to Bobby, as well as a Guest, who requested a letter from John to Bobby specifically with the purpose of thanking him, but also being mad at him. This letter was probably written around when Dean was about 13 or 14, and Sam was about 9 or 10. I want to thank Leia 96, mb64, flygirl33, the guest WomanOfLetters, jojospn, kjdw, a Guest, and knwinchester for their awesome reviews. :D And thanks to all who read these!  
**

**Disclaimer: I don't own _Supernatural_.  
**

_Bobby,_

_ I want to take a moment to thank you for everything you've done for me and my sons recently. I know that you're busy, and you have hunts of your own, and that it's never exactly convenient for me to drop my kids off on your doorstep. So I am grateful that you have been so willing to spend the time and effort helping us. But I also want to say I am sincerely ticked off that you find it alright to do whatever you want with them when I'm not around. _

_ I get it. I'm leaving my kids with you, and it's a favor, and I shouldn't make more demands on top of that one. But honestly, you treat them like babies when I'm not around! You take them to the park to play catch, and you let Dean fix junkers with you instead of training, and the last time I showed up Sam was watching freaking cartoons! They don't need to spend their days with childish activities and relaxation. They need to be honing their skills because one day they're going to need them. _

_ You of all people should understand why it's so important for them to be prepared for the reality of what's lurking in the shadows. You know that monsters don't hold back just because someone is untrained, and they certainly don't hold back just because someone wanted normalcy instead of hunting. And that's what you're doing. You're trying to give them normalcy, but you're ignoring everything they need to do to stay sharp as hunters. _

_ Newsflash: Hunters aren't normal, and my sons are hunters. This world isn't even normal, and the faster they realize and accept that, the better things will be. You're only giving them false hope when you let them skip out on training to watch some game on TV with you. You're only fueling Sam's irrational belief that he can have an average life someday. And you're confusing Dean by making him doubt that his brother can't get out someday. _

_ You know they both begged me the other day to stay at your place instead of the motel, just because we were within a hundred miles of Sioux Falls? And I realized right then it's because they'd rather have the break they get with you than the training they get with me. And it kills me, because they just don't see that I'm trying to help them. That I love them, and I'm doing what's best for them. _

_ You get the easy job. You get to be all nice and relaxed with them, and they like you for it. Hell, I know they even love you for it. But me? I get such a bad rap for being controlling and demanding and harsh. And it's all because I'm actually trying to protect them! Trying to make them strong enough to stay safe in this messed up world. _

_ I guess what I'm trying to say is this... You'd be making my life a hell of a lot easier if you'd just make them stick to their training when they're with you. I know you want them to relax because they're "just boys". But they're my boys, and I would do anything to keep them safe. Even if it means vilifying myself by making it so they can't come around your place anymore. So please, Bobby, don't make it come down to that. I just want them training, because I just want them safe. I hope you can see and respect that. And I hope one day they'll see it too. _

_Sincerely,_

_John _

**Secondary Author's Note: Thanks for reading! I am still working on several requests, and am always open to even more! Also, reviews are greatly appreciated. :D  
**


	26. If There's Anyone

**Disclaimer: This letter contains spoilers for the seaosn 8 finale (8X23 "Sacrifice")! Do not read if you haven't seen that yet! Also, I don't own _Supernatural_. **

**Author's Note: This letter is for mb64, who requested a letter from Dean to Sam responding to Sam's confession in the season eight finale. I want to thank ClassyMuse, mb64, shirleypositive72, jojospn, a guest named GuestJ, Leia 96, kjdw, and a guest named WomanOfLetters for their awesome reviews. And a big thank you to all of you who read these!  
**

_Sammy,_

_ First I want to apologize, because I've been too hard on you and I'm only just now seeing that. I've been too busy bitching and moaning about things you've done wrong, or things you haven't done, or even things you just could have done better… And what I haven't been doing enough of is telling you how proud of you I am. You say you're biggest sin is letting me down? Well I think you're free of sin then pal, because you haven't let me down Sammy. Not really. You've always been the one to pull through and save the day. Yeah, we've had our rough patches, and I'm not saying you've never done anything wrong. But you've never dropped the ball and let it sit there either. You fix your mistakes, and you always come through in the end. _

_ Sure, you teamed up with Ruby. But you held her in place when I ganked her too… And after you broke the last seal, I remember you chose to bow out of hunting for a while. Even when I was making it all about 'trust', you chose to be honest with me and let me know you weren't up for it. I might've been pissy with you at the time, but that doesn't mean I didn't respect your decision. I was impressed that you were man enough to admit your weakness, and do your best to overcome it. _

_ And I know you feel bad about me getting turned into a vampire while your soul was gone. Sammy, I don't blame you for that. You had no soul! The only reason that hurt me back then was because I didn't know your soul was gone at the time. I just thought that Hell had changed you. And you know what? I didn't get mad at _you_ for that. It hurt because it was _my_ fault. Because I freaking helped you jump into that pit, so anything you did afterward was on me. _

_ And I am proud of you for how well you handled Hell once your soul was back. Yeah, you had Lucifer hallucinations coming out your ears for a while, but you never once did anything evil because of it. Sam, I was an irritable, frustrated, dangerous wreck after my time in Hell. But you stayed good, and just kept fighting to save people, even when your hallucinations were driving you insane… I admired that. I really did. _

_ Then there's Purgatory. Now I know I said you should ask God's forgiveness for that…but to be honest Sam, I don't think you not searching for me was sinful. I wasn't being fair when I got mad at you for that, and I know it. Yeah, it hurt me to hear that you didn't try and find me. But that doesn't mean you were evil for not torturing yourself trying to get me back. You didn't have a clue where I was and had no way of knowing I was even still alive. And I did make you swear you'd move on if something like that happened... I guess it just hurt because in Purgatory, getting back to you was what kept me going. I kept imagining the kid I practically raised, lost and scared without me there. And that image gave me the strength to fight my way out of that wasteland… _

_ But the reality is that you aren't a little kid anymore Sammy. You aren't even lost or scared. And if I was to be entirely honest about how that makes me feel, then I would say it makes me proud. Because you've grown into such an incredible guy. You've overcome all of your mistakes and chosen to risk everything to save the world, again. You were right to be the one to take on the Hell trials, even if you did end up having to let them go…_

_ Because you're the one with the strength to admit your mistakes, humbly apologize for them, and try again. That's the kind of man who would deserve to save the world from Hell. That's the man I'm proud to know. You're a good man, and your conscience deserves to be clear even without some stupid confession. And I want you to know I believe that firmly. Because if there's anyone in the world I trust Sammy…anyone I know I can turn to…it's you. Always. _

_Dean_

**Secondary Author's Note: Thank you so much for reading! Reviews and requests are always welcome. I have a growing list of requests, and I'm loving it! :D **


	27. Dear Mr Wyatt

**Author's Note: This is a letter written for a guest named 'GuestJ', who left a review saying, "In the episode After School Special Mr. Wyatt asked Sam if he was happy. Sam didn't answer and it made me sad. Please have Sam write his answer to Mr. Wyatt..." So this is a Letter from Sam to Mr. Wyatt after "After School Special" in season 4. Obviously, Sam tiptoes around a few points in this letter that he can't be very blunt about, like Dean's trip to Hell for example... So please don't think I'm breaking canon when you read this. I'm just pretty sure Sam wouldn't want to share the whole truth here... lol I want to thank mb64, SPNxBookworm, and the guest called GuestJ for their recent reviews, and to thank all of you spectacular readers! :D  
**

**Disclaimer: I don't own _Supernatural_. **

_Dear Mr. Wyatt,_

_ I finally have an answer to your question. You asked me the last time we spoke if I was happy, and I wasn't really sure how to respond at the time. Now I am. To put my answer simply: Yes, I'm happy. However, I don't think that kind of simplicity makes for a good enough response, so I'll elaborate…_

_ All of my youth was spent frustrated and angry because life was hard, and my family didn't seem to care that I felt the "family business" only made it harder. Like any teenager, I responded with rebellious behavior and general attitude problems. I fought a lot with my dad, and I eventually walked out on him and my brother. _

_ When I did, I finally got to live the kind of life I had dreamed of. I got into Stanford University and was getting straight A's. I was set up to go to law school after receiving a pretty high LSAT score… Everything was where I thought it should be in my life. And then everything changed. My girlfriend passed away, and I went into a sort of downward spiral. My brother came to my rescue, and was there for me through my emotional recovery… Then we lost our father, and it was my turn to be there for him. _

_ And after our father's passing it seemed like life just kept getting harder again. I had put my pursuit of a law degree on hold completely and was back in my family's line of work. The business was…failing, so to speak. Or at least it was getting out of control. Everything was falling apart, and then my brother got very sick. He went through a period of time where he was... I guess 'absent' would be a good word for it. I really thought I had lost him, and it almost destroyed me. _

_ But he bounced back. It was miraculous, honestly, and I couldn't have been more grateful for the positive change of fate. And suddenly my perspective changed too. True, my life has taken some twists and turns, and I am on a path that's very different from the one I had hoped to take in life. I'm still working in my family's business and I am definitely not attending law school any time soon. And life is still as confusing and hard as ever...But I have my brother, and we have our health. And we have a list of good memories that top the bad ones. Even on days when it feels like the world is balancing on the edge of a knife, and everything might fall apart at any moment, we still manage to crack jokes and smile. _

_ I guess I just finally grew up, got over my frustration and anger, and accepted that life doesn't always work out the way you planned it would. However, that doesn't mean life is bad. I'm finally able to see how the little things I used to take for granted are really worth a lot. I've grown to appreciate everything I do have. And I'm happy with all of it. _

_ So thank you for prompting me to think about where I'm at in my life and how I feel about it. You really are a great teacher, and I'm glad our paths crossed again. _

_Sam Winchester_

**Secondary Author's Note: Thanks for reading! I welcome both reviews and requests. :) **


	28. Unrequited

**Author's Note: This is just a fun letter for ClassyMuse, who wanted to see a letter from "crazy lady Becky". Therefore, I was prompted to write this letter from Becky Rosen to Sam Winchester, taking place shortly after Season 7's episode "It's Season Seven, Time For A Wedding". (There is a brief hint at Sabriel talk in here. Absolutely nothing dirty at all, I swear. However, I thought Becky might say something about it since she is clearly into slash fiction on the show...) Thank you to kingdommast, ClassyMuse, reannablue, flygirl33, and mb64 for their most recent reviews. And a giant thank you to all of you readers!  
**

**Disclaimer: I don't Own**_** Supernatural.** _

_To My Dearest Sam,_

_ Ok, so I know I'm the last person you want to be getting a letter from after our recent encounter. But I swear this isn't just some love letter written in a fit of hormonally induced obsession with my one true love who just hasn't realized yet how perfect we are for each other… Well, maybe the very last part is true, and I hope one day you see that we would be great together. But more to the point…_

_ I need to apologize again for basically drugging you into marrying me. That's not how healthy relationships start, and when ours does start, I want nothing more than for it to be healthy. It was my mistake to do that to you, and I promise to be more patient from now on. Your love for me will take time to mature, and I am prepared to accept that now. _

_ This letter is also to thank you. You didn't need to save me from Guy. You could've left me to "get what was coming to me". Instead, you fought that demon off and saved my soul. Now, I know you believe that you did it because of your deeply engrained need to save people, especially when it risks your own life. But I also know something else. I know you had a secret motive for saving me that even you couldn't comprehend at the moment, but that burns deeply within your heart…_

_ You saved me because you care about me. About us. You couldn't help but risk your neck to keep my soul where it belongs. Here, on Earth, waiting for you. And Sam, words cannot express the gratitude I feel for your hidden internal devotion to me. _

_ One day, when we're married and have five children who all are named after your deceased loved ones, because I know you're the kind of sensitive man who will do that…And one will definitely be named Gabriel because even though you'll have picked me, I've read the fanfiction on you guys, and I admit I can see the spark you two shared briefly. And I'm ok with that. I won't judge... _

_ Anyway, I'm off topic. I guess I'm just saying that when we do end up together in the brightly shining future I see for us…We'll be happy. Because I'll finally be with you, and you'll have finally come to see that the love we share is stronger than anything, including demons like Guy. So until that wonderful day, I leave you to struggle to come to terms with your affection for me, while I wait patiently. _

_This love of mine shall not remain unrequited forever. But for now I accept that you need time to comprehend the depth of our connection. So I will say is this, again: I am sorry I couldn't wait, and I am ready to wait now. And thank you for saving me. Your buried love for me is savior enough, but my soul being safe on Earth is definitely a bonus. _

_So I guess this really did turn out to be mostly a love letter. I just couldn't help it, because the love I feel for you is so strong that no force in existence, supernatural or other, can destroy it. I will end on this note: I am waiting patiently for you to awaken and smell the roses of our love Sam. Or in this case, the Rosen.  
_

_With Everlasting Love, _

_Becky Rosen _

**Secondary Author's Note: Thank you so much for reading! Reviews and requests are like sunshine rainbows...Always welcome. :D**


	29. Jess

**Author's Note: This one is for the guest named WomanOfLetters, who made a request a while back for "a letter from either Dean or Sam to one of the girls they had a relationship with". So, this is from Sam to Jess, written some time in season one after Jess's death. I want to thank jojospn, SPNXBookworm, ClassyMuse, mb64, and Leia 96 for their most recent reviews. And thanks to all of you incredibly wonderful people who read these! **

**Disclaimer: I don't own _Supernatural_. **

_Jess,_

_ I owe you an explanation. After everything, the very least I can do is try and explain to you why you were murdered. It was all because of me. Because I'm not normal. I never have been and am relatively certain that I never will be. Remember when I told you my mom died in a house fire when I was a baby? It wasn't an ordinary fire. She died in a fire just like the one that killed you. _

_ I was in my nursery, and something evil broke in, and my mom came to try and protect me and the thing murdered her. It pinned her to the ceiling and lit the room on fire. My dad managed to save my brother and me, but he couldn't rescue my mom. He watched her burn, like I watched you burn. _

_ And it drove him mad with grief, so he vowed to avenge my mother's death by hunting down the thing that took her from him. From us. And so he became a hunter of all the nasty creatures that go bump in the night. See, they're real. Practically all of the monsters you hear about in stories and legends are actually out there preying on innocent humans, and my dad learned everything he could about them all. He made it his mission to hunt each of them down until he could finally find the thing that killed his wife. And as my brother and I got older, he taught us everything he knew. He raised us into the life of hunters. _

_I knew how to put down ghosts, kill a werewolf, and take out a wendigo by the time I was thirteen. I was a better shot than most military sharp-shooters. I could read ancient books written entirely in Latin, because a lot of valuable information comes out of dusty old tomes. I could stitch up wounds received in the "line of duty", and believe me when I say I needed to do it pretty often. The kind of jobs we worked rarely ended without some form of injury. _

_And so my dad, brother, and I became very efficient hunters, and yet I wasn't able to enjoy the kind of life we lead. In fact I hated it. I wanted nothing to do with monsters and hunting. I wanted to go to school, and get a regular job, and have a wife and children. I wanted to be normal. So when I found out I had been accepted to Stanford, I ran away. I had a shouting match with my father and I just walked out, abandoning him and my brother. I came to California and focused on my education. I made friends and I studied hard. I met you. And for a while there, everything was perfect. _

_ And then Dean showed up and said our dad was missing. Remember when Dean said our dad was on a hunting trip and hadn't been heard from in a few days? Yeah, that was a bad sign because obviously he wasn't hunting Bambi. So I left with Dean because I felt obligated to try and help him find my father. I felt obligated to help my dad too, if it came down to it. _

_ But I should never have left, because there was something else coming, and much as I'd love to say I couldn't have known anything bad would happen to you, I'd be lying. _

_ Jess, I had these awful dreams the week before you died. I saw you burning. I saw you dying. I saw it all, and I would wake up terrified and just bristling with the feeling that something big was coming. _

_And yet I still left with Dean. _

_ How could I do that to you? How could I leave you so defenseless? I never told you about the real me, and I should have, because I should have known that after living so long as a hunter something bad was always just around the corner waiting to strike… But it's more than that._

_ I should have paid attention to those dreams because I knew they weren't just nightmares. I knew there was something horribly wrong. And I ignored it because I wanted to be normal. Because I wanted to pretend that nothing bad could happen because I had left all that behind me. Instead, I ended up leaving you behind me to die a terrible death when I could have saved you just by being there to protect you. Like I was trained to do. _

_ Out of all the people I've saved, you're the one life that probably mattered most, and I failed you. I should have saved you Jess, and I am so incredibly sorry. I should have stayed behind to keep you safe. Honestly, I should have never had you move in with me. That would have been the surest way to protect you. _

_ Because clearly I'm not meant to have a normal life. Since I was a baby death and destruction have followed me. I'm not normal. I'm a freak. And freaks should never grow close to people, because those people will only end up hurt. It's as if you were dead the moment I asked you out to that first dinner… _

_ I swear I will avenge you. I've accepted that I can't be normal. I've accepted that I'm a freak. But I will at least be the freak who ends the thing that hurt you. I know it can't bring you back, and it kills me inside to know that nothing I do will actually make a difference. But I'm still going to take the bastard out. Because I owe you so much, and that's basically the least I can do. I love you Jess. And I'm so, so sorry. _

_Sam_

**Secondary Author's Note: I know this was a kind of downer letter, but I still thank you for reading it! I am working on many letter requests right now, but I definitely welcome more! Also, reviews make my day. :) **


	30. Respective Roles

**Author's Note: This one was written for ****SPNxBookworm**, who requested, "After doing the first trial, Sam writes a letter to Dean. Maybe concerning the fact that Dean almost got chewed off to hell by Crowley's hell hound...again." So here it is! (It's a little similar to the theme of a letter I wrote before called "The Light I See", but I did my best to make it at least somewhat different. At any rate, this letter would have been written by Sam before he wrote that one...) I want to thank jojospn, juliewrites13, WomanOfLetters, mb64, ClassyMuse, QuestJ (sometimes called GuestJ), a Guest, SPNxBookworm, TG, and knwinchester. Also, thank you all who read these! 

**Disclaimer: I don't own _Supernatural_. **

_Dean,_

_ I know you're not exactly happy with me right now. Actually, I know that you're mostly unhappy with yourself right now, and that's why I'm writing this. To tell you that it isn't your fault, and I don't blame you, and I am honestly glad it was me that killed that hellhound. For so many reasons. _

_ The first and probably most important reason would be that you were scaring the crap out of me with your talk about me living some white picket fence life after you get yourself killed doing these trials. You made it out to be a glorified suicide attempt Dean, and I couldn't let you do that. I just couldn't stand by and let you run off to your death, because it takes a will to survive in order to actually survive these kinds of things and I'm kind of horrified that you don't have one. So I'm doing the only thing I can think of to keep you going right now. I'm putting myself in the line of fire. Me doing these trials means that you will feel obligated to stick around and back me up. And if that's the most I can offer to keep you breathing at this time, then I'm sure as hell going to do it.  
_

_ My second reason is less logical but equally relevant in my eyes… Do you have any idea what it's like to watch you get ripped apart by a hellhound Dean? Because I can tell you that I do. Unfortunately I could give you every single disturbing detail of what that looks like. Because I've seen it before and it's amazing that I'm sane at all after watching that happen. I still have nightmares about it sometimes, did you know that? I wake up sometimes and have to actually look over at the other bed and see you sleeping there, just to remind myself that you're back. That you aren't lying in ribbons on the floor and that I won't have to bury you again anytime soon._

_ Except that's exactly what I thought I was going to have to do. The moment you swore you were going to go after that hellhound yourself, the post-traumatic stress kicked in and all I could think was "Not again. Oh God please not again." I know you wanted to protect me from whatever these trials might involve…But Dean, nothing could be worse for me than to watch you go up against another hellhound. Last time I had to just watch, and I couldn't do anything to stop it…But this time I could do something. I could fight it myself. _

_ So then I ran after you and saw it clawing at your stomach… And I'm telling you there's not a thing in the world that could have stopped me from killing it right then, because I swore to myself I would never again stand by helplessly while one of those things ripped you up. I can't put into words how relieved I am that I kept that oath. How glad I am that you're safe. _

_ I guess my final reason is the least logical, but it matters to me. I feel like doing these trials gives me a chance to make up for past mistakes. I've done so much wrong in my life, and it feels like closing Hell might be a way that I can clean my slate. I'm sure it will be nearly impossible…But hey, we've faced worse odds before, right? Of course, the key term there is 'we'. _

_ 'We' have always come out on top. 'We' have always managed. And I think this is how it has to be, because otherwise the one of us who took these on would fail. If you were doing it alone, you'd just be killing yourself with it and hoping to go down swinging. If I did it without you to help me through, I'd probably just veer off course and mess up again. No. It definitely has to be us together, in these respective roles. Me killing the hellhounds and whatever else, and you giving me the strength I need to do it. _

_ So in that sense Dean you are completing the trials. Because as much as I'm certain that I can do this…I am equally sure I can't do it without you. Basically, it's not your fault. I chose this, and I stand by that decision. And I'm grateful because I already know you'll stand by me. _

_Sam _

**Secondary Author's Note: Thank you for reading! I am so thrilled because I have a huge list of requests I'm working on for these. Feel free to review, and I promise I still welcome even more requests! :D  
**


	31. I'll Do My Best

**Author's Note: I survived finals! :D Now that my irrelevant announcement is out of the way...lol This letter is for kingdommast, who requested a letter from Dean to Sam responding to my third letter in this series "Constant". (which was a letter from Sam to Dean after going off to Stanford) I suggest you read that letter first if you haven't yet... Anyway, I want to thank mb64, jojospn, knwinchester, GuestJ, kingdommast, SPNxBookworm, and Emile for their awesome reviews. And thanks to all of you awesome readers!  
**

**Disclaimer: I don;t own _Supernatural_. **

_Sammy,_

_ So you're taking some pretty fancy classes, huh? Philosophy, government… Sounds like the kind of stuff I'd only find useful as a sleep aid. Honestly, I don't trust the government. They're either fully aware of all the crap that hides in the shadows, and are therefore asshats for not doing a better job of protecting their public, or they're a bunch of idiots who haven't caught on to what's really out there. Either option keeps my opinion of them at an impressive low. And what could a philosophy class possibly have to offer a guy like you? Does everyone just sit around discussing their deepest thoughts? Actually, that sounds right up your alley, Mr. Share-And-Care. _

_ Ok I'm sorry… I know I'm totally ripping into you and your classes here. I don't mean to, it's just it sucks, you know? You were damn right I felt "torn" when I got your letter! Dude, you had the shouting match of the century with dad, and then you just ran off. One day I had my brother, and then next day he was across the country fully planning on never coming back. Do you know what that felt like? Actually, you do. You said so in your letter. "I know you feel like I betrayed you." Betrayed is a pretty good word for how I'm feeling. But you're right about the other thing too. Much as I hate to admit it, I don't want to lose touch with my pain in the ass preppy college boy brother…_

_ Even when he's telling me that part of why he's worked so hard to get into an IV league school is so that he can set an example for me. Who's the older brother in this relationship anyway? I was pretty sure it wasn't you._

_ Sorry, I'm picking on you again. The truth is, reading that letter made me kind of understand. I wouldn't want to watch you die either Sam. And much as I miss the crap outta you, I'm actually kind of relieved that you aren't chasing monsters anymore. Sure, you're far away. But you're safe. And from the sound of things you're happy too. I guess that matters most to me. Actually, I know it matters most. _

_ And by the way, I never realized that you had such a bad reaction to that werewolf hunt I got injured on. I mean, I'm perceptive and I definitely noticed you started acting different after it. But I guess I always thought that seeing me get clawed up made you realize how dangerous the job was for you. Not how dangerous it was for me..._

_ You know you don't actually have to worry about me, right? That's not your job. Yeah, I'm going to keep hunting things, because it's what I do. But my true job, the one I've had practically my whole life, is to do whatever I can for you. And if me being alive and kicking keeps you happy, then I swear I'll do my best. I'll be careful like you asked. I'll use my "great" brain. And most importantly, I'll keep you posted so you know I'm ok. And that has nothing at all to do with me wanting to also make sure that you're ok by communicating with you…Nope. Not a thing. _

_ I get frustrated with you Sam, but I also understand you. Just like you seem to understand me pretty well. So here's to you becoming a fancy lawyer, and me being around to scream embarrassing things from the crowd at your graduation. Until then, have fun with your classes…Bitch. _

_Dean_

**Secondary Author's Note: Thank you for reading! I am neck deep in all of your requests right now and I love it! Reviews and more requests are definitely welcome. :D**


	32. You're Welcome

**Author's Note: This letter is for mb64, who made a request a while back for a response letter from Bobby to John regarding my 25th letter "Newsflash". (I suggest you read that letter first if you haven't already.) I want to thank judyann, reannablue, jojospn, mb64, kingdommast, and SPNxBookworm for their awesome reviews. And my thanks to all of you wonderful readers! **

**Disclaimer: I don't own _Supernatural_. **

_John,_

_ First, I want to say you're welcome. Helping your boys is always a pleasure, and I never mind you dropping them off with me for indefinite lengths of time. However, I am "sincerely ticked" at you for having the nerve to scold me for what I do with the children you're not paying me to look after. Don't get me wrong, I adore having Sam and Dean around here. But for Pete's sake… _

_ You say I "treat them like babies" when you're not around. Has it slipped your brain that neither of them is even pubescent yet? They deserve to be treated like the kids they are. At least every once in a while! It isn't like I never train with them at all. I take them to practice their shooting and I have them study the lore. I just don't make it the only thing they're doing around my place. I try and offer them some sort of balance. Isn't that something you should want for them? _

_ Yeah, when you showed up last time Sam was watching cartoons… Did you know the boy had a fever of one hundred and two the night before? It broke sometime early in the morning, and I was letting him relax a bit because he had been up most of the night sick. Of course, I know he kept his mouth shut about that because he didn't want you to flip out on him. _

_ And Dean is damn good at helping me fix those junkers. If you're going to hand me your kids for weeks on end with no compensation, at least let me put them to use! Heck, the boy actually likes to fix engines and radiators. So I let him. You know how many fathers would be proud to have a thirteen year old who could repair the cracked chassis on a '68 Mustang? I dare you to find me one other than you who wouldn't… _

_ And yeah, I get it. You want to keep them sharp so they're never caught off guard by one of the nasty creatures lurking in the night. Wouldn't it be safer to just keep them away from hunting at all? They know what's out there, but why do they have to seek it out? People like you and I, we were already old when we got into this life. But John I've got a "newsflash" for you. Your sons are just boys. Not men, and not warriors, but boys. And I'll tell you something else. They won't be boys for much longer. Dean is getting taller by the minute, and Sam is already mature enough to have philosophical debates with my neighbors. _

_ I'm telling you John, if you don't give them some semblance of a childhood now, you'll miss your chance completely. So train them if you feel you've got to, but cut them some slack every once in a while. Because that's all I'm doing John. I'm just giving those two kids the breaks they've earned. _

_ And you know what? I think you've got enough of a need for my "services" that you won't actually follow through on your threat to keep them away from here. So suck it up pal, because as long as they're under my roof, they'll get to have those little moments of peace. Dean can fix all the muscle cars he wants, and Sam can watch freaking Marry Poppins if it's on. And you'll just have to learn to deal. Because they might not be my sons, but they're staying at my house, so I get to treat them as such while they're there. _

_Bobby _

**Secondary Author's Note: Thanks for reading! Reviews and requests are always appreciated. :D **


	33. Someone Who Will Never Happen

**Author's Note: This is a letter for shirleypositive72, who gave me perhaps the most unique request I've gotten so far: "What about a letter from now-Dean to future-Dean (from The End)?" So here it is. A letter from Dean to his future self from "The End", written probably shortly after that episode took place. I want to thank judyann, kingdommast, jojospn, juliewrites13, flygirl33, mb64, ClassyMuse, GuestJ, and SPNxBookworm for their incredible reviews. You guys pushed me over 200 hundred reviews this last chapter, and if I could hug you all, I would. :D And thanks to all of you wonderful readers, without whom, this series wouldn't be around. :) **

**Disclaimer: I don;t own _Supernatural_. **

_Someone Who Will Never Happen,_

_ I'm a bit drunk here and I felt like ranting about some of the stuff I can't talk to Sammy about. Because yeah, there's no way in Hell I'm gonna tell him about the kind of ass I became in the future. Even though he really wouldn't be one to talk, seeing as he had chosen to let the devil wear him as a meat suit and all… But really that was my fault, wasn't it? Or at least it was your "my" fault. _

_ You let him go. Not even that. You friggin' pushed him away to the point where he would rather let Satan drive than keep living his own life. You abandoned him when he needed you most, just because you were pissed and self-righteous. But what else is new? Honestly, like you've never made mistakes? Like the start of the apocalypse wasn't equally your fault? But typical you, you chose to judge Sam and send him away. And what did it get you in the end? Hell on Earth, that's what. _

_ I guess I'm glad I saw it. Much as I hated what I saw, and hated you, and hated me for apparently becoming you… I don't know. It was an eye opener. Not the one that dearest Zach wanted me to get, but it was good for me all the same. I got to see my flaws and what they could lead to. I got to see the consequences of my actions, and I got to come back and make a better choice. Because in the end, seeing me as you…Seeing what a dick I'd become… I still understood. Because after you died I saw Sam. Well, Samifer ... Anyway, it clicked._

_ He's why you were such an ass. You had to go about every day defending an indefensible cause, the whole time knowing Sam was out there somewhere trapped inside his own head while Lucifer used him to wreck the world. And you knew it was your fault because you'd abandoned him. You chose not forgive him and he suffered for it. And so you suffered for it. And in the end, you didn't care about anything anymore. _

_ I know Lucifer didn't overpower you in that garden. I know you died because you couldn't do it. You couldn't shoot Sammy even when he wasn't Sammy anymore. So instead you gave up and let him kill you. It's ok, because I'd have done it too. I mean, I'm sure you know that. But yeah… _

_ Wow this booze is really kicking my ass. Or maybe it's just that writing a letter to the future version of you that you're going to make damn sure never exists is a pretty effed up subject, and my brain feels drunk just thinking about it…Anyway, I thought I'd tell you that I made a different choice than you, and I think it'll fix things. I can't guarantee it'll stop the apocalypse. But I can promise that now it won't start because you let Sam down. _

_ Because I didn't. I got back to 2009 and immediately called his giant ass up and told him to come back. Whether he hooked up with a demon or not, he's still my brother. Much as he can hurt me sometimes, I'd still do anything for him. I've got to be there for him because it keeps him on the right track. And maybe more importantly, he keeps me good too. As long as I've got Sammy to look out for, I know I'll keep fighting my hardest. I know I'll stay sane and strong. I know that I won't die because the first time I'd seen my brother in years was as a Lucifer puppet. I might still die, but I'll die by Sam's side. Where I belong. And at least he and I will still be us. So thanks for being such an ass. It made me less of one. _

_A Better Me_

**Secondary Author's Note: Thanks for reading! Again, hugs all around for you amazing people who got me to break 200 hundred reviews. I'd never dreamed of it when I started writing these, and I can't thank you all enough. :D (Needless to say more reviews, as well as requests, are still very welcome.)  
**


	34. Adam

**Author's Note: This letter is for juliewrites13, who requested, "A letter from either Sam or Dean to Adam probably expressing regret over not being able to save him from his death or the fall into the pit. Or even being able to get to know him, even if he was just a half brother." I chose Sam, because I figured he'd have some guilt over getting out of the pit when Adam didn't. I want to thank jojospn, judyann, a Guest, kingdommast, shirleypositive72, reannablue, and SPNxBookworm for their recent awesome reviews. And thanks to every one of you readers! **

**Disclaimer: I don't own _Supernatural_. **

_Adam,_

_ So I barely know what to say here, but I know I need to say something. Because I got out. I got out and got my soul back, and you're still stuck in that cage with them both. So I guess I'm writing this out of survivor's guilt, but it just feels like I've got to. _

_ I want to talk to Dean about you. I want us to remember you because you deserve to be remembered. Just because we didn't know about you before doesn't mean we don't care. But I can't talk to Dean about this. He's Dean, and he can't handle feeling responsible for another little brother's trip to Hell, you know? _

_ Actually, you don't know. You don't know Dean, or me, and you barely knew dad...And it's awful because you should. You should have known us, and we should've been there to help you. You should never have been dragged into the whole apocalypse mess. If we had just known you were out there, we could've gotten to you before Zachariah did. We could've stopped Michael from taking you. We might've even been able to show you that we weren't the jerks they both portrayed us as._

_ I owe you my still having Dean, did you know that? Because you said "yes" to Michael, they stopped tormenting Dean. He was free to do whatever he needed to do, which in this case, was go on a suicidal mission to be by my side after I let Lucifer in. And you know if it weren't for him showing up, I wouldn't have had the strength to take back control and jump in that pit. I wouldn't have been able to stop everything from falling apart. So more than just me owing you for Dean, I think the world technically owes its safety to you. You freed Dean up to come give me the push I needed, and that made it so the world could be saved. You saved the world Adam, I just wish you knew it. _

_ And I wish you'd gotten a better reward. Honestly, I hate myself for being the one who made it out of that cage. Why me? I have done nothing but screw up and bring crisis to the world. But you never did anything wrong. You were never given a choice, like me. You never made the wrong choice like I did. You just got stuck being born half Winchester. But that's enough to screw up your whole future, trust me… _

_ You know, I always wanted a little brother? I used to see the way Dean lit up whenever I looked up to him, and I wanted that for myself. I wanted a little kid to idolize me the way I did Dean. To want to be around me. A kid who I could show the ropes to. Maybe not all the same ropes Dena showed me. I still think he'd have been better at giving you dating advice, what with my track record compared to his… But I could've shown you other things. Like maybe I could've helped you with school, or picking a career, or even something stupid like shaving. Anything would've been good...  
_

_ Knowing you were out there most of my life and I just didn't know it...It makes me just plain sad. Because it feels like I was robbed of something priceless. I lost something that can't be replaced, and I didn't even know it. Not until it was way too late. _

_ I'm sorry Adam. I'm sorry I never knew you. I'm sorry that all you know of me and Dean is that we bring trouble to innocent lives like yours. I'm sorry we couldn't protect you better. I'm sorry you got stuck in that cage. I'm sorry you didn't get out instead of me. I'm so, so sorry._

_Sam_

**Secondary Author's Note: Thanks for reading! Reviews and requests bring a smile to my face. :)  
**


	35. After I'm Gone

**Author's Note: So this letter is for SPNxBookworm, who gave a me this great prompt: "Dean's deal is almost up. He's scared to go to hell and he knows that Sam isn't coping so well. He isn't sleeping and won't eat. All he does is research on how to get Dean out of it. A few days before his deal is up, Dean writes a letter for Sam." So here it is! I guess it is pretty similar in theme to a letter I wrote before called "The Best Thing", but I still liked the suggestion too much to say no. :) I want to thank kingdommast, jojospn, ClassyMuse, Leia 96, judyann, mb64, GuestJ, and SPNxBookworm for their awesome reviews. And thank you to all of you who are reading these!  
**

**Disclaimer: I don't own _Supernatural_. **

_Sammy, _

_ I've been so proud of you for so many years. You grew up from the tiny kid that followed me around doing nothing but firing questions at me, into such a smart, nice, giraffe of a little brother… You know that when I came back for you at Stanford and saw the life you had built for yourself there, I was impressed. Because the little kid who used to confuse toothpaste for sunblock when he was four, and who needed to call me for dating advice when he hit high school…Well he had grown up and become a pretty awesome dude. Even after everything that happened with Jessica, and Dad, and Azazel, that man was still there. And I was…am…so proud of him. But I'm terrified that I'm losing him. _

_ I'm scared man. I'm more scared than I've been in my life… Well no, that's not entirely true. I remember when you got stabbed and I was holding you knowing full well that I couldn't stitch that wound up and make it all ok. And that feeling of helplessness frightened me more than any Hellhound ever could. So things could definitely be worse… But I still feel scared. And you want to know the surprising thing? I'm not scared of Hell. Ok I am scared of Hell, but that isn't the biggest thing I'm freaked about right now. You're what's scaring me Sam._

_ You and the way you don't sleep, and barely eat, and basically do nothing but research ways to get me out of the mess I'm in. I see the potential in you for you to go completely crazy after I…after I die. I have to say it, because it's going to happen. Sammy, I know you're trying your hardest, but I don't think saving me is possible. And I'm ok with that, because I made this choice and I would do it again in a flash. But I am not ok with you losing yourself afterwards._

_ I want you to be alright after I'm gone. In fact I don't just want you to be ok, I need it Sammy. I always have, and that's what got me to this place. So just promise me you'll be alright. I know you'll grieve, but just swear you won't do anything stupid? And don't you give me any of that crap about how saving me isn't stupid. No Sam. Saving YOU wasn't stupid. Saving me by un-saving you would be. I wouldn't thank you for it, that's for sure. You know I'd only run right out and sell my soul all over again anyway, and the cycle would never end. _

_ It needs to end. So that you can go on and live a real life. No more all night demon research, no more seeing how long you can go without eating before the malnutrition kills you. Just life and you living it to its fullest. I did this so you could live Sammy, not so you could kill yourself with guilt and grief. I've said it before, but I'll say it again: This isn't your fault, and it isn't your responsibility. I'm a grown man and I made my own decision. A decision that I stand by firmly. _

_ So Sam please, just let it go. Let me go. And let yourself go. Not in the way you're currently doing where you let your health and mental state go. I mean let yourself go forward in your life. Go to a new college, or meet a girl and get married, or just go do anything that isn't dwelling on what happened to me. I wouldn't want anything else for you, and you know that. So Sam, I'm begging you here… Please stop killing yourself over me. Please live for me instead. So I know that after I go you'll still be the little brother I've always been so proud of. _

_Dean_

**Secondary Author's Note: Thanks for reading! Your reviews and requests make my day! :D **


	36. Dr Phil

**Author's Note: So this letter is for GuestJ, who gave me this very interesting suggestion: "How about a letter from Dean written anonymously to Dr. Phil expressing how he feels about lying to Sam about killing Amy?" I thought it sounded challenging, so of course I had to do it. :)So here is a letter from Dean to Dr. Phil taking place about a month after 7X03 "The Girl Next Door". I want to thank jojospn, mb64, reannablue, kingdommast, judyann, ClassyMuse, GuestJ, and SPNxBookworm for their awesome reviews. And thanks to everyone of you who reads/has read these! **

**Disclaimer: I don't own _Supernatural_. **

_Dr. Phil,_

_ Aside from the fact that I feel crazy just writing you this letter, I also have some stuff I think is weighing me down and I might benefit from your input. You're supposed to help people deal with their internal emotional conflicts and all that crap, right? Well I'm feeling pretty darn conflicted inside right about now. I'm hoping you can help. _

_ So I've got this brother, you see. He's a good guy. The best kind of guy actually, and I've practically raised him since he was a baby. (And no, I'm not trying to toot my own horn when I follow up "he's the best" with "I raised him".) Anyway, we're in the same line of work. We work in…um…basically pest control. Only for the really nasty pests that are a hell of a lot more dangerous than your average ant or roach thing. So we do this extermination work together, and we pretty much always have. In all our years working together, we have never really had a problem agreeing that the pests we take care of need to, well, be taken care of. That is until recently. _

_On this one gig about a month back he wanted to protect the thing that we should have killed. In fact, he made me agree I wouldn't do anything at all to hurt it. I don't know what made him suddenly go all soft hearted, but he's my brother, so I agreed. Only I went behind his back and finished the job anyway, because someone had to do it... But instead of feeling good about a job well done, I only feel like I've done something terrible. What am I supposed to think?_

_ I mean, I know I shouldn't feel bad for this particular pest. It had been putting lives in danger. Heck, I actually know that it took a few lives before I killed the thing…But I feel like killing it was still wrong. Like by doing so, I hurt my brother. Even though he doesn't even know what I did! _

_ I guess that's what's bothering me, huh? I'm keeping a secret from him and I hate that. We've kept secrets from each other before and it never ends well. In fact it almost always ends really freaking badly. This one time he kept a secret about this chick he was dating…But more importantly, he kept it a secret that she'd made him start doing some pretty heavy drugs. Needless to say, that one spiraled out of control quickly. He only barely got out of the situation with his life. _

_ He's not the only one who's tried keeping skeletons hidden in their closet. I've kept secrets from him too. One time I tried to hide it from him that I'd made a pretty bad business deal. One that would definitely screw me over eternally… Anyway, I didn't tell him because I wanted to protect him from it. In the end he was only more pissed at me because he figured out on his own what I'd done, and was furious I hadn't trusted him enough to tell him…And he was upset I didn't let him try and help me.  
_

_ Jeez, we sound like a couple of teenage girls when I try explaining all of our drama! You know what though? This helped. I mean I'm totally never sending you this letter…But writing it helped. I finally figured it out. It's not what I did that's bugging me. I know I made a good call. It's the fact that my brother is going to be pissed and hurt that I broke my promise to him. That's what's clawing me up inside… I don't want him to be upset with me, because I don't like when we're not on good terms. I guess that's why I should tell him sooner than later, so he's less pissed than if I wait. I also suppose that's why I'm not going to say a thing to him about any of this, because the minute I do he'll be at least some level of pissed, and I can't handle that right now. _

___Damn this whole guilt thing sucks. _

___I just don't know how to break it to him without risking pushing him away, and I can't lose him right now. I need him too much. _

___Yup. Definitely time to find my zippo. This girly letter is toast. _

**Secondary Author's Note:**** Thanks for reading! Reviews and requests are greatly appreciated. :D **


	37. January Twenty Fourth

**Author's Note: Firstly, I want to apologize for not posting yesterday like I usually do. For some reason I was unable to login to my account all day...I'm not sure if it was my computer or the website, but it is all better now! :) Secondly, this letter was not requested by anyone. But I kind of got inspired recently and I had to write it. This is a letter from Sam to Dean, written on January 24****th**** the year that Dean was in Purgatory. I hope you like it! Also, I want to thank jojospn, mb64, GuestJ, flygirl33, jusyann, reannablue, and SPNxBookworm for their recent incredible reviews. And thanks to all of you equally incredible readers!**

**Disclaimer: I don't own **_**Supernatural**_**.**

_Dean,_

_ So it's January twenty fourth today. And you're gone. I thought I'd be able to handle it, you know? I thought that after everything I'd at least be prepared to face the day and survive it. I wasn't fooling myself trying to imagine enjoying it. I knew I couldn't do that… But I thought I might be able to get up and go about my day, and maybe even do it without breaking down crying. _

_ I was wrong. I can't even bring myself to get out of bed. So I'm sitting against the headboard you'd call girly, writing you a letter that you'll never see, because I need to feel close to you today. It's stupid, right? I mean, it's not MY birthday. Why should I feel down that it's not being celebrated? Maybe it's because I'd give up every single birthday I've ever had for a chance to give you yours today. _

_ That's not what you'd want to hear and I know it. After all, you gave me some pretty awesome birthdays when I was little and it'd be terrible of me to throw them away. I know you'd be offended after all the effort you put into them. Because you always put me first. _

_ Remember the year of the epic cake? I definitely do. I remember how I always used to get a cupcake or something small from the store on my birthday. I never got a full on cake because Dad saw it as a waste. I guess he was right, because we couldn't exactly store the leftovers. But when I was seven I cried because some kid in my class told me how he got a two layer cake for his birthday, and I wanted to have a special cake too. _

_ Well, Dad dropped us off at Bobby's for my birthday that year and you sent me on a scavenger hunt all around the junk yard to find my present. I thought the hunt itself was pretty cool, and it definitely kept me busy for hours. Which is exactly what you wanted, of course._

_ When I finally found the last clue and followed it back to the kitchen, I found that you and Bobby had made me the largest and messiest looking cake I'd ever seen. It was a whole three layers tall and I didn't care in that moment if it was falling apart or not. It was the best cake I'd ever laid eyes on in my life. To this day I remember that as my second favorite birthday present. _

_ Of course it's only a close second to that year you told me you were dragging me to a strip club to celebrate my twenty fifth… I wanted to smack you, but you just shoved me in the car and told me to "relax". I was pissed because you totally know how uncomfortable I get in strip joints, and I couldn't believe you'd force me into one on my birthday. And then we pulled up in a grass field in the middle of nowhere, and you parked the car and said, "We're here!" _

_ And you laughed because apparently the look on my face was "priceless" when I finally realized you'd been messing with me. You'd actually packed our cooler with beers and picked a spot with a great view of the sky. And we sat on the hood of the car for hours just talking and drinking. Just being brothers, I guess. And it had been so long since we'd done something like that…It was perfect. _

_ Who's going to just be my brother now? There isn't anyone in the world that could do it. Not one person. You're the only guy who could ever be my family like that, and now you're gone. And now I'm stuck here alone failing miserably at not thinking about the fact that it's your birthday, and you're dead. So Happy Birthday Dean…_

_I really miss you. _

**Secondary Author's Note: Please accept my apologies if I stabbed your feels with this one. Lol But thanks for reading! Reviews and requests are totally welcome. :D **


	38. Wouldn't Know Me

**Author's Note: This letter is for juliewrites13, who suggested a while back that I write a letter "from Dean to Lisa & Ben shortly after he decided to walk out of their lives forever." So here it is. I want to thank jojospn, SPNxBookworm, reannablue, mb64, ClassyMuse, kingdommast, judyann, and GuestJ for their awesome reviews. And thanks to all of you wonderful readers!  
**

**Disclaimer: I don't own _Supernatural_.  
**

_Lisa,_

_ I'm writing this letter because I sure as hell can't say all of this to you. Not now. You wouldn't believe it or trust it. You wouldn't even know it was me if I came to you. I mean you might know that I'm the guy who "hit your car" and landed you and your son in the hospital, but you wouldn't know it was…You just wouldn't know me._

_ You know when I first met you, I just wanted sex. I was a drifter passing through yet another town, and the bar where I met you was just another pick-up spot for me. It's a hard job I do, and sometimes I just needed to flirt mindlessly with a hot chick to unwind. And if I ended up taking her back to my motel, even better. You were a hot chick and I unwound. We ended up back at my motel room. And yeah, better doesn't even begin to describe it… And then we went our separate ways, and I honestly thought nothing of it. Not until after I sold my soul. _

_ Then I found you for the second time. I met Ben and I swear, I really thought the kid was mine. It shocked me, but it didn't upset me. A guy like me should've been running for the hills, but all I could think was "Wow. I'd be lucky if he was." But you said he wasn't, and the job pulled me away from you again anyway. But the second time I left you was different. I thought about you a lot after that second visit. About you, and Ben, and the life I could never build with you both but really wanted to. Damn, I had really wanted to stay. But I was going to die in a year, so I didn't have much choice. I had to leave. _

_ The third time I came to you I was staring down an angelic possession shaped gun. I was getting ready to say yes to an archangel and give up on life, but I wasn't going to do it without saying goodbye to you. You, the random hookup from years ago. The girl with a son who wasn't mine and no reason to feel particularly attached to me. But I had to see you because I was attached. You and Ben were important to me, even when my own future wasn't. I told you that when I pictured myself being happy, it was with you guys. And I meant it. But I had to leave, and it made you cry. And I should've left you at that and not hurt you anymore. But Sam had me promise that after he jumped into Satan's cage I'd find you. I'd build something good with you and Ben, and I'd keep going. So I did. _

_ I showed up in your life for the fourth time and you took me in. The emotionally broken man that I was, you took me and cleaned me up. You helped make me better. You were with me through the drinking, the nightmares, and the pain. You were the life-raft I couldn't let go of. So when Sam showed up, I couldn't just walk out on you. I left with Sam, but I still stayed with you… Eventually we did break things off. There was no way to keep up the pretense that I was being an attentive partner for you. I was living on the road hunting monsters and risking my neck daily. You were at home hoping I wasn't dead and explaining to your son why his not-exactly-father wasn't home, but still loved him. It was a mess, and it was for the best that you both got out of it._

_ Except then the demons found you and Ben. They took you and hurt you. You got possessed, and you were stabbed. You were dying, and seeing you lying in that hospital bed fading away… I knew what I had to do. What I should've done years before, but was too damn selfish and afraid to commit to. I had to leave you forever, but this time I needed to make it permanent. I needed to be the one to die, so to speak. So I made my friend not only heal you, but erase your memories and Ben's. I had him take me from every corner of your recollection of anything. _

_ So now I might as well be dead to you, but you're definitely not dead to me. You and Ben are the family I always wanted and never deserved. The wife and son I would have loved with everything in me, but that would have died because of that love. The one-night stand and the not-even-legally-adopted kid who I would have given everything to, and in the end gave everything for. Because you were both everything to me for a while there. My family, my home, and my tether to sanity when I was falling apart. And I had to let you go. _

_ I am glad you don't have to be aware of any of this because I think it would only hurt you more. But I wish with everything in me you could know, just for a moment, how sorry I am. How much I loved you, and how much I miss you now. But you don't, because if you saw me tomorrow you wouldn't know I was…You wouldn't know I had even been yours. You just wouldn't know me. _

**Secondary Author's Note: Thanks for reading! I know this was a slightly downer letter, but I couldn't see Dean writing anything cheerful on this subject, so I apologize if this made anyone feel sad. :P Like always, reviews and requests are very much appreciated! :) **


	39. Count You As Friends

**Author's Note: So this letter is a long time coming. mb64, this is for you. :) You have requested a letter from Garth multiple times, and I have always found it really hard to get his "voice". Unfortunately, I can't promise that this one really captures it, but I figure it's now or never...so here goes! This is a letter from Garth to both Sam and Dean. I want to thank jojospn, juliewrites13, m1tchells, judyann, mb64, SPNxBookworm, GuestJ, and WomanOfLetters for their recent amazing reviews. I also want to thank all of you who read these. You are all incredibly amazing, and I love you. lol **

**Disclaimer: I don't own _Supernatural_. **

_Gentlemen,_

_ I wanted to thank you both again for helping me with the shojo gig. I wouldn't have been able to get the job done as neat and tidy without you guys, so you deserve my gratitude for that. But more than just helping me with the job, I want to thank you for being so warm toward me. As I'm sure you both know already, but this line of work doesn't lend itself much to a blossoming social life…and the few connections you do make always seem to be rough around the edges. But you two just seem like really good guys, and I'm glad to count you as friends. _

_ I had a lot of fun kickin' back and drinking a beer with you, not to mention the company on the hunt was nice. Living a life like this is hard. I learned a long time ago to appreciate the little things, because nine times outta ten they're all you're going to get. A hot tub, an apple-tini, and maybe a night off with my lady friend… These are the things that keep me going. But heck, having a couple of cool dudes to chillax with once in a while definitely makes my "things that keep the job worth doing" list too! _

_ You know, I've wanted to have a partner for this job before, but I just never seem to find the right fit. Maybe it's because I'm more of a "lone wolf" kind of guy by nature, and long term hunting partnerships aren't really my thing. So when Bobby first called me up to suggest working with you Dean, I wasn't immediately keen on the idea. I guess it's ironic that the job is lonely, but I don't necessarily get excited for company. Anyway, those were my first thoughts on things. But then I met you Dean, and I liked you. You seemed like a pretty genuine guy, and definitely a good hunter. Sometimes you meet hunters who you wonder how they aren't dead yet, but you're definitely not one like that. I could see you've got skill, and I was more than willing to help you out. _

_And now, after the shojo thing, any hesitation I had about either of you is totally gone. I want you to know I'd be more than happy to hunt with you guys again in the future. Not always, of course. I don't think that would work for any of us. I mean, I can see you've got the whole "brothers to the end" thing down-pat, and you don't need someone butting in messing up that flow.  
_

_ But I'm just saying…If ever you need a hand on a job, give me a call. I think you're nice guys and it was a real pleasure working with you. If you need me for anything at all, don't hesitate to let me know. With a job like this it's not often you get to have someone watching your back, but I'm letting you know right now: I'll watch your backs any day. _

_ This life may be rough, and it might be pretty anti-social most of the time, but that's why when you do find a good person to trust, you should definitely trust them. And I have a feeling that I can trust you both. So here's to future hunts together! Let's hope the next monster doesn't leave us with a hangover the next day, eh? _

**Secondary Author's Note: Thank you for reading! Your reviews and requests are much appreciated... I have an idea for what I'm doing for letter 40, but I'm running out of requests to fulfill, so feel free to pile them on! :) **


	40. Because You Prayed

**Author's Note: So when I wrote my 20th letter, I finally wrote one from Castiel to Dean. Well I figure that, in celbration of doubling that number today, I would write another Castiel letter. This time the letter is from Castiel to Sam, and I imagine it was written some time shortly before Castiel returned the souls to Purgatory. I want to thank Leia 96, jojospn, judyann, ClassyMuse, shirleypositive72, SPNxBookworm, and mb64 for their recent awesome reviews. And thank you so much to everyone who reads these! **

**Disclaimer: I don't own _Supernatural_. **

_Sam,_

_ I want to thank you, because you prayed to me. After everything I have done to you. After I carelessly destroyed the wall that was supporting your mental stability. After I opened Purgatory and threatened to slaughter you, Bobby, and your brother. After I made you bow to me… You still prayed to me. And it was not a prayer of anger, manipulation, or spite. You prayed to me in an attempt to help me. For the faith you clearly have in me, I cannot express my gratitude enough. _

_ Then again, I must recall that you have always been the one with faith. I remember when I first met you, I had heard so many things about you. I had heard of your tainted blood. I had been told of Azazel's desire to use you for blasphemous deeds. Not to mention I was fully aware of your involvement with the demon Ruby at the time of our first encounter…_

_ And yet when I met you the entire negative stigma that had been attached to you seemed to dissipate in my mind. For what I saw in you was not a man who sought to rule the world, or who wanted to use demonic abilities to destroy God's Earth. I saw a man brimming with admiration and respect for the angels he had prayed to his whole life. Uriel did not see this, nor did the others who met you. But I did. _

_ I regret having called you "the boy with the demon blood" when I first shook your hand. I did not understand at the time how much pain that would cause you. But I saw it in your eyes as soon as the words left my vessel's mouth. You didn't want to be known for the foreign blood within you. You wanted to be known for all of the good things you had done or tried to do. And in that instant I knew that you could not possibly be the monster that Heaven feared you would become. You were simply too good. Whatever you were doing with the demon, it must be a mistake. Your eyes held no malice. Your soul though twisted with grief and suffering, was still pure. You were a good man then, and a good man you have remained to this day. _

_ You have the ability to forgive, and that is the mark of a kind person. You forgave me for my atrocities. You offered up a prayer to me like a lifeline. You asked for me to return to you and your brother. Not so you could scold me, trap me, or defeat me. You only wanted to help me. I suppose you could relate. You had, once upon a time, gotten carried away with the consumption of a powerful substance. Demon blood, souls, what's the difference in the end? They both bring power and with that power, destruction. You were trying to save me from that destruction. Even after I had failed to save you, and even after I broke your internal wall._

_ You are a true friend Sam. I know you believe I care more for your brother. And although I admit I have felt more responsible for Dean's well-being since I raised him from Hell, and that he and I do share a strong bond of friendship…That does not mean that I do not value the friendship you have built with me. _

_ Especially now, when everyone has turned their backs on me, including Dean. Rightfully so, because my sins are great and unforgivable… _

_ Still, you give me hope. Because in one simple prayer you offered me the forgiveness I don't deserve. The forgiveness I needed in order to find the strength within myself to attempt to right these wrongs. _

_So thank you Sam Winchester... The man with kindness in his soul. _

_Castiel_

**Secondary Author's Note: Thanks for reading! I love you all with so much love. lol Your reviews and suggestions are definitely welcome. :D **


	41. Smith

**Author's Note: This is a letter based on a request PMed to me a while ago. ClassyMuse sent this to me, labeling the request as "crazy". How could I say no to a challenge like that? lol The request was for "Letters to either Sam Wesson or Dean Smith". (From season 4's "It's A Terrible Life", in which Sam and Dean are working in an office building with no recollection of their real lives, and are living like normal people. Zachariah is responsible, and that's the episode you first meet him in.) Anyway, I chose to write one from regular Dean to Dean Smith. This is what came of that choice. :)I want to thank kingdommast, m1tchells, shirleypositive72, judyann, jojospn, WomanOfLetters, and SPNzBookworm for their awesome reviews. And thanks to all you great readers!  
**

**Disclaimer: I don't own _Supernatural_. **

_Dear Dean Smith,_

_ I can't believe some angel actually managed to temporarily erase my entire life from my memory. What the hell did he think that was going to prove? Did he really think that making me into a fancy business guy who suddenly discovers he can swing an iron crowbar at ghosts was going to convince me that hunting is "who I am and I love it"? Or whatever crap he was spewing... _

_ If anything,he showed me what a great life I could have if I didn't have the shitty one I'm stuck with. I mean yeah, being you meant that I ate rabbit food for lunch and dinner and dressed like a freaking suit-catalogue model…But you had a nice apartment! Hell, it was an amazing apartment. You had a giant TV, an excellent view, and there wasn't a single questionable motel stain in sight. _

_ You had a pretty normal job too, and I actually liked it. I got to be the boss in a situation that wasn't risking my neck every second. I woke up in the morning and had a really nice coffee, and I drove to your really nice office, and I did your really easy job. Because really, what could be easier than sitting on my ass all day calling business friends and instructing employees on the proper procedures for filing work reports? _

_ But still…There was something missing. I know this Zachariah dude wanted me to think it was hunting. That I was lost without a creature to kill. And yeah, I guess when I did finally get on the job it felt right... But I don't think hunting was what I was lacking most. _

_ I think I was just missing Sam. Looking back on it, I realize that the moment I saw him in the hallway, even with no memories at all…I felt connected to him. Not just that, I trusted him. I opened up to him and immediately felt ready to work at fighting some ghost alongside him. And the whole time I didn't doubt once that this guy who, as far as I knew I'd just met, was going to have my back. _

_ Now that I'm back to being me, complete with my dangerous job and my endless string of scuzzy motel rooms…I see the lesson I think I needed to learn. That no matter what my life circumstances are Sam makes it better. _

_ I loved my comfy life as you. But when I started hanging around Sam 'Wesson', I was willing to consider giving all of it up to travel around the country hunting monsters with him like an idiot. Because deep inside, I knew I'd give up all the luxuries in the world to have Sam by my side. And now with all of my memories back in order, I still feel that way. I'd give up everything just to have my brother. So although Zach was using you to show me what a great life I have as a hunter, all he really showed me was that life could really good without hunting…Except it would never be 'great' without having Sammy by my side. _

_ I think that should scare this feathered jack-ass. Because honestly, how many jack-asses have Sam and I faced together and NOT maimed and/or ganked? Angel or not, this sucker is still perishable. And if it comes down to it, I know Sam and I can finish the job. So I guess Zachariah is right. The job is awesome and I do love it. But only because it's our job; Sammy's and mine. And we do it together. _

**Secondary Author's Note: Thanks for reading! This one was a bit off the wall, but I couldn't resist. lol Reviews and requests are always welcome! :D I also want to let people know that it is likely I won't be posting tomorrow because it is Father's Day in my area. I wouldn't be a very good daughter if I spent the day pouring over fanfiction. I would just be the kind of daughter I am every day of the year _except_ for Father's Day. lol  
**


	42. Not Like Most

**Author's Note: So this letter is for mb64, who made a request a while back for "a letter from teenage Dean to John for father's day". Well, Father's Day was yesterday in my area, so I felt the timing was right to do this one. :) So here is a letter from Dean, who I'm going to say is about age 13 here, to John for Father's Day. I hope you enjoy! I also want to thank jojospn, SPNxBookworm, judyann, mb64, kingdommast, ClassyMuse, Angel of Nightfall, GuestJ, and WomanOfLetters for their recent awesome reviews. And thanks to all of you great readers! :D **

**Disclaimer: I don't own _Supernatural_. **

_Happy Father's Day Dad!_

_ For Father's Day I know most kids get their dad a card that says something cute like, "To The World's Best Dad", or, "To Superman…AKA My Dad". I'm not that cute and you know it. But neither are you, so I think it's safe to say you won't be receiving any lame Hallmark cards from me this year. But that doesn't mean I don't think you deserve something for the day. I just think you've earned something a little more sincere, so here goes…_

_ Dad, you have always done your best to take care of me and Sam. Yeah you've put us in some pretty dangerous situations with all the hunting, but never without putting yourself in the line of fire first. And the hunting itself…You've done an amazing thing by making sure Sam and I know about this stuff. Most fathers get told on Father's Day that they do a lot for their family, but you've done a heck of a lot more than most, and I want you to know I can see that.  
_

_ You don't just protect your sons. You dedicate yourself to making sure those sons can protect themselves too… And I'm grateful to have a father who is willing to sacrifice his time to make sure I know how to properly disarm an assailant, or how to read a Latin rite to exorcise a demon. You know, one of my favorite memories is of that time when I was seven and you spent a good five hours teaching me how to hit a bull's-eye with my first pistol. I was a sucky shot at first. I mean I was basically awful. But you didn't pick on me over it or give up on me. You just stayed there with me while I practiced over and over, until I finally hit the target. and you looked so happy after I did, it made my day. _

_ Shooting, grappling, exorcising demons… There are skills that most dads would never dream of teaching their kids. And even if they knew about monsters they probably wouldn't teach their children about them anyway. And I bet lots of people would say that's because children don't belong hunting. But that's just a load of crap designed to excuse them from having to spend the time teaching their kids how to defend themselves. They get to avoid exerting the extra effort, all under the pretense that it's to "keep their kids safe". That's just a heaping pile of bull-shit. Keeping them safe would be arming them with the skills and knowledge to handle any situation. Keeping them safe would be exposing them to the real world, and then showing them how to deal with it. You definitely keep us safe, both by looking out for us, and by showing us how to look out for ourselves. And you deserve to be appreciated for that. _

_ So I want you to know that it really does mean a lot to me. Everything you've done and continue to do…It's a ton of work and you don't ever get rewarded. Heck, society would actually probably punish you if they knew the kind of stuff you let Sammy and I do. But it's because of all of that stuff, and all the work you put in to raising me and Sam…That's why I'm proud to call you my dad. _

_ So Happy Father's Day. You aren't like most dads. In fact you aren't like any other father I've met, but I'm glad of that. Because to me, you're better than the rest. _

_Dean_

**Secondary Author's Note: Thanks for reading! I genuinely appreciate each and every review I have received, so please feel welcome to share your thoughts on this letter or any of them I've written with me by leaving a comment. Also, Requests are always great! :D  
**


	43. The Better Brother

**Author's Note: This letter is for kingdommast, who suggested a while ago that I write "a letter from Sam to Dean thanking him for forgiving him for hooking up with a demon." I hope this fulfills the request adequately! I want to thank jojospn, SPNxBookworm, mb64, flygirl33, kingdommast, judyann, GuestJ, and applepieisnice for their recent awesome reviews. And thanks to you incredible readers! :D**

**Disclaimer: I don't own _Supernatural_. **

_Dean, _

_ I know I've been over this, but I'll say it again. I was a stupid self-righteous jerk. I didn't listen when you told me not to use my abilities. Or whatever you want to call the dark things that I can do. I ignored your request. I said it before…That was basically your dying wish, me not going down that path. And I just went ahead and did it anyway. You have every reason to hate me for that. But you don't. You got furious, rightfully so... But you clearly never hated me. You showed up and tried to win me over toward the end there. You fought your way back to me, even after I beat the crap out of you over Ruby. _

_ And I still can barely believe the ferocity with which I defended her. That monster in a woman's body…I let her become my priority even though my own brother was begging me to trust him. And even though he had never once given me a reason not to put my trust in him, I still withheld it. I trusted a demon instead. And of course that ended badly. Why wouldn't it?  
_

_ But you never turned away from me. Even when we went our separate ways after everything was done and Lucifer was free. Even when I said I wasn't sure I was in control of myself around demon blood yet and needed some time away from the job. And I know you wanted that time away from me, because I had really hurt you… Still. You called me on a nightly basis. And every time you did I knew it was to check in and make sure I was safe. _

_ I mean the first words out of your mouth each call were "So are you doing ok Sammy?". Not, "have you fallen off the wagon yet", or, "have you been thinking about demon blood lately". Nothing even close to that. Just a simple question, completed with embarrassing childhood nickname, that illustrated the concern you've always shown for me. Was I ok. _

_ And I wasn't. I felt like the biggest ass that ever lived. Hell, I deserved to feel that way Dean. What I didn't deserve was a brother who, despite having been betrayed by me, still cared enough to call every single day. A brother who never once hung up when I said I needed to talk, even though he knew I needed to talk about how I was hurting from the same crap I had done that hurt him. You still listened and did your best to make me feel better. _

_ Of course you never actually said, "Sam, it isn't your fault." That would've been stupid and we both would have known it was untrue… But you did call me up and crack your patented Dean Winchester lame jokes. You would talk late into the night about my boring day at the bar I was busing at, or whatever other regular things you could think of. You never initiated a talk about hunting. It was still a wound for you. But I got the feeling you knew it was for me too. And you wouldn't hurt me with it. Even though you had to have wanted to, you never once did. _

_ And I guess that I'm just grateful, man. I know I said thank you already but I don't feel like you really understood. I don't think you actually got how appreciative I really am. So I'm trying again to make you see how much it meant to me. To make you see that your forgiveness genuinely mattered to me. And I meant it when I said I wouldn't let you down. After all, you let me back in. After everything I did to you, you still let me come back. I owe you for that. _

_So thank you for clearly being the better brother. I promise I'll do my best to be a better brother to you.  
_

_Sam_

**Secondary Author's Note: Thanks for reading! Reviews and requests are very much appreciated. :) (As a side note to kingdommast: I didn't really focus on the literal implications of the term "hooking up", because I doubted the original intent of your request was for a letter about Sam's guilt regarding just the sex... lol I hope I was right!)**


	44. The Just-Plain-Old Brother

**Author's Note: This letter in for A Guest who signed their review "TG". TG requested a letter from Dean responding to my most recent letter, "The Better Brother", where Dean expresses his own guilt for the way he behaved leading up to Sam opening the cage. This is what I ended up with. :) I want to thank kingdommast, reannablue, mb64, the Guest "TG", judyann, jojospn, SPNxBookworm, and GuestJ for their recent amazing reviews. And thanks to all of you wonderful readers! **

**Disclaimer: I don't own _Supernatural_. **

_Sam,_

_ You have a pretty weird definition of 'better', you know that? I mean don't get me wrong... If you had called me the more handsome brother I would have had to agree… But better? Absolutely not true. In all seriousness Sam, I wasn't any better than you through all of this. I got pissed at you for the things you were doing, but that doesn't mean that I wasn't stumbling along my own twisted path the whole time. In fact, reading your letter made me realize just how damned screwed up I was to you this past year. Hell, I've been messing things up for you longer than just that… _

_ See, I know I screwed up big time because I just couldn't let you grow up. Yeah, I'm finally admitting it. You're a full grown adult man, and I've been a little slow on that uptake. Because to me you only grew to be about twelve. Not a day older than that. I mean, I look at you and still see the little kid who used to need me to scare off bullies, because he was too friggin' nice to kick their asses like he could. I still see the boy who couldn't figure out how to ask a girl on a date, and needed me to give him advice. I look at you Sammy, and I see the little brother I spent my whole life trying to protect and keep innocent. _

_ I did a sucky job, seeing as I roped you into hunting again… I guess I was always too selfish in the end to let you go completely. Partly because I felt like I needed to have an eye on you to know you were safe. Partly because I needed to have you around so I felt like I had a purpose. _

_ Because you've always been the thing that gave me a purpose. Hunting is something I do, but you have always been my life. I died for you, and you know I'd do it again. I said it before, and thank God you don't have to remember this moment like I do… But I told you once that it's always felt to me like I had one job. One. And that job was keeping you safe. _

_ I guess I was too busy protecting you for the sake of fulfilling my own messed up needs to actually look at who you are. To see that you don't really need that protection anymore. If I had stopped for five minutes I might've realized that you grew up a long time ago, and all my attempts to shelter you were only smothering you. That you were bound to rebel against the constant babying eventually. _

_ So you know what? In the end, this wasn't entirely your fault. I'm your brother, and I've spent most days with you for the past 26 years. I should have seen what all of my "protection" was doing to you. You even tried to warn me, and I was too set in my ways to listen. Hell, maybe I even heard you but didn't want to admit that you don't need me like that anymore. Because if I did…Well I probably wouldn't even know what to do with myself. Like I said, you were my life. If I didn't need to watch out for you all the time, what else was there for me? _

_ So I'm sorry Sam. Because in that sense I put myself first and it pushed you toward some nasty stuff. I'm not going to pretend that you had no choice. We both know you had choices along the way, and you made some pretty crappy ones… But I am saying that I can see that I contributed to what lead you to make those choices. I get it that you wanted to feel independent and strong, because everything I did always made you feel like a little kid. _

_ Well from here on out, I promise to do my best to treat you like the man that you've become. I won't tell you that I'll stop trying to protect you. We live a dangerous lifestyle, and I'll be damned (again) if I'm going to throw you out there fight monsters alone… But I can tell you that I'm going to be more respectful of your capabilities. You're not twelve. You're a twenty six year old hunter, and you deserve to be treated as such. _

_ I'm not "the better brother". You're my equal Sam, and we are equally responsible for all of this shit. So let's just move forward and clean up our mess like always, shall we? _

_The Just-Plain-Old Brother_

**Secondary Author's Note: Thanks for reading! Reviews and requests are always appreciated greatly. :) **


	45. Answers

**Author's Note: This letter is for reannablue, who gave me a very challenging suggestion. She requested a letter from Sam to Sarah's daughter after episode 8X22. This letter is in the top three hardest requests I've ever attempted to fulfill, so thank you reannablue for having challenged me so much. :) (Needless to say, spoilers are contained for season 8 episode 22, AKA "Clipshow". I would strongly advise you not read this if you haven't watched that episode yet!) Anyway, I want to thank reannablue, judyann, kingdommast, applepieisnice, mb64, the guest "TG", jojospn, WomanOfLetters, and SPNxBookworm for their awesome reviews. You guys all helped me break three hundred reviews yesterday, and I couldn't possibly be more grateful! Also, a big thanks to all of you amazing readers! :D **

**Disclaimer: I don't own _Supernatural_. **

_Dear … _

_ I don't even know your name. Your mother died in my arms, and I don't even know your name… I'm sorry. I really am, because she'd be here if it wasn't for me. See, a long time ago I met your mother at an art auction. I was hunting for a cursed painting, and she was unwittingly selling exactly what I was hoping to destroy. Well some stuff happened after that and to make a long story short, I ended up saving her life from a homicidal ghost. _

_ And your mother ended up saving me in a way too. I had lost someone I really loved, almost a year before I met your mom. I had lost the woman I had wanted to marry. And then I had closed myself off from the world, and wouldn't even consider dating. Your mom changed that. She helped me "crawl out of my warm, safe shell", as she would have put it. We didn't end up staying together after the job was over with… But she had saved me from the depressive and self-destructive path I was on. And like I mentioned, I had saved her from the evil spirit. _

_ And that should have been the end of it. It should have been a happy ending. Not necessarily a fairy-tale ending, but definitely a good conclusion to a series of events that could have ended horribly for both of us. But that wasn't the last of it. And God, I wish it had been…_

_ Our happy ending was just a trick. Years later, a demon who knew way too much about my history figured out that I had saved your mother once, and so he used her against me. He threatened to kill her if I didn't stop trying to kill him. I was stupid. I thought I could protect her from whatever lackeys he sent to attack her. I drove hundreds of miles to come to her rescue. My brother and I, we holed up in her hotel room with her and laid out every defense imaginable. We were both prepared to fight for her. Hell, I would have been willing to die for her, because I sure wasn't prepared to let her die because of me. _

_ But I had misjudged the situation. I expected the demon to send his monsters. Instead, he simply cursed your mother by stashing a hex bag in her room ahead of time. She died in front of me, and my brother and I were mere moments too late destroying the hex bag. _

_ I was too late to save her. _

_ And so I'm writing this to you because I think you deserve to know the truth. I spent my whole childhood fighting to figure out the truth about what killed my mother. In fact, the entirety of what remained of my family dedicated their lives to finding and killing the thing that took her from us. I am writing this to you so that you don't have to spend your life hunting for answers like we did. _

_ I'm giving you the answer right now: She died because of me. Like everybody I love seems to die because of me. The demon cursed her, but she was marked for death from the minute I walked into her life. I guess was the original curse. I am the man who can't get too close, because the people I love all seem to suffer for it later. So if you want to blame someone, blame me. I didn't physically murder your mother, but I am the reason she died. _

_ I also want to let you know that I am trying to make this right. I can't bring her back, but I am trying to make sure that demons like the one that killed her can never again hurt anybody else. And it very well might kill me, but that's ok. I'd rather die trying to make amends for all the pain and loss my existence has brought to the world. I'd like to end my life knowing that I'd avenged Sarah. I'd rather go down knowing that, in death, I was fighting for her daughter to have a chance to live in a safer world. So here's to you. _

_ I am genuinely sorry I destroyed your past, but I am ready to give literally everything to ensure for you a better future._

_Sam Winchester _

**Secondary Author's Note: Thanks for reading! I wanted to add that, despite my excitement at recently having reached more than 300 reviews, I don't do this just for the numbers' sake. I want you all to know that reading your individual reviews makes me genuinely happy. The kind and supportive things you all say...My own words could not express how much it thrills me to see my work appreciated by such a wonderful bunch of readers. And that is what really keeps me writing. So thank you all so so much! :D (Needless to say, reviews and requests are very welcome. lol) **


	46. Changed

**Author's Note: This letter is for a Guest who requested "one from Dean to Cas when he went all godly". It took me a while to get to this one, so sorry for the wait. :P I want to thank SPNxBookworm, jojospn, GuestJ, kingdommast, judyann, lilliannaelizabeth, reannablue, mb64, and WomanOfLetters for their awesome reviews. And thanks so much to all of you who read these! :D  
**

**Disclaimer: I don't own_ Supernatural_. **

_Castiel,_

_ Man, it's been an awfully long time since I've called you that. I honestly think it's been years. You've just been 'Cas' to me for so long now. Not 'Castiel: Angel of the Lord'. But Cas, the socially awkward badass in a flasher coat. Cas, the rebel who gave up everything for humankind. Cas, my friend. Only you aren't anymore. You aren't my friend, and you just aren't Cas._

_ You've changed. A hell of a lot, too. I guess it's less of a change, and more of a regression. You've regressed to a different time when you were just another tool in the Heavenly Host's shed. Then again, back when you were just another mindless drone, I don't think you'd have swallowed Purgatory. But hey, who am I to say I know what you would or wouldn't do? I clearly had you all wrong from the start._

_ Because honest to God…Sorry. Honest to You… I would never have guessed you would do something like this. If someone had told me a year or two back that you would team up with friggin' Crowley and crack open Monster Land, I would have told them they were nuts. Hell, I did! When Bobby and Sam first doubted you, I told them, "No Way. This is Cas we're talking about. He wouldn't do something like that." Well I must win the 'Biggest Idiot' award…_

_ Apparently, I never knew you at all. Because that's exactly what you did. I tried to warn you. When it finally hit me that you were actually working with a demon…I tried so damn hard to convince you to stop. I bared my soul and told you that you were like another brother to me. Guess that wasn't smart, seeing as stealing souls is kind of what you're into now, huh? And you just looked at me with this cold expression and told me to back off. I can see why you need souls, because you clearly don't have one of your own…_

_ A fact that became incredibly obvious when you busted down Sam's wall. I mean really? How the hell could you do that?! You were his friend, man. You were our family. And you betrayed me in a way that I really don't think can ever be fixed._

_ I actually think it hurt less when Sam hooked up with that Ruby bitch, because at least he could blame the demon blood a little. I didn't see any substance abuse driving you to do any of this. Of course now I guess you actually are hyped up on monster mojo, so you're being an even more massive dick…_

_ Well you know what? Fine. Be as stupid and cruel as you want. Me and Sam, we'll bow out. We won't do a damn thing to save you from yourself. And when it all comes crashing down around your ears, because you have to know it will…I hope you're happy knowing that you gave up your chance to have someone stand by you and help you fix it. Because I would have. I said you were family to me, and I think I've made it pretty obvious over the years that I am willing to do a hell of a lot for my family. Sometimes literally even Hell. Not like that kind of loyalty would mean anything to you, clearly. _

_I hope it was all worth it for you. _

_And I'm still a giant idiot, because I still hope you're ok in the end. _

_Dean _

**Secondary Author's Note: Thanks for reading! Your reviews and requests are always appreciated immensely. :D  
**


	47. My Boys

**Author's Note: This letter is for a Guest, who suggested "a letter from Mary to the boys". However, it is also for GuestJ, who suggested "A letter to John from Mary during episode 5.13 The Song Remains the Same". In my head, Mary wrote this letter in their brief down-time before Michael and Anna showed up. I want to thank ClassyMuse, reannablue, SPNxBookworm, judyann, jojospn, shirleypositive72, mb64, and GuestJ for their recent amazing reviews. And thanks to all who read these! **

**Disclaimer: I don't own_ Supernatural_. **

_My Boys,_

_ I am writing you both a letter because I have enough of a history with hunting to know the odds aren't very good of my still remembering our encounter if we all survive this. But I want to remember. At the very least, I want you to remember… And I want you to know some things. Things I apparently never got to tell you…_

_ First, to my youngest: _

_ Sam. You are named for your grandfather, who was a hunter and good man. And much as you are clearly a hunter, it is the later adjective I would say describes you best. When I look into your eyes, I see so much kindness. I see hurt and loss too, which pains me immensely. I would never have wished for my children to suffer through everything that you and your brother have been through…_

_ But even though I can see in your eyes that you are haunted by grief and dark memories, there is a light that shines within them too. You have a certain softness about you that I admire. You are gentle. Now, please don't misinterpret me. I know you are a man, and a hunter, and you would never want to be called 'soft'. But by that, I don't mean you are weak. Not by any sense of the word. I see strength in you. Greater than that of almost any man I've met. In fact it is equaled only by your brother. _

_ But contained within you is a level of empathy that most hunters don't possess, let alone a hunter who has lived through the kind of events that you have faced. And I think that it's amazing. That YOU are amazing. I'm telling you Sam, value that quality in yourself, because it's worth a lot. And be proud of it, because I am certainly proud of you. _

_ Now for my eldest:_

_ Dean. The first time you came to 'visit' me, you warned me about November 2__nd__ of 1983. And I get it, because that's the day I died, right? But the fact that I died that day isn't what scared me. It was the agony held in your eyes as you begged me to stay in bed on that day. The pure pain you felt as you thought about it. And now, knowing that I'm your mother… I feel an even stronger pang when I look in your eyes. _

_ You hurt each time you see me, because I am the mother you lost. I was taken from you, and I see that you would give everything and anything to save me. I want you to know that I don't necessarily believe I can be saved. As I'm sure you're aware, what with having grown up a hunter…Things don't really work out that smoothly for people like us. I can't just trust that I will escape my fate so easily. Although I am so grateful that you cared enough to warn me. So if I don't end up surviving that night, I want you to know, I am so proud of you. _

_ Seeing you all grown up…. I had always imagined what it would be like to have a son. I imagined a cute child, or a gawky teenager, or even a strong young man. Not once did I imagine the person that knocked on my door yesterday. But I count myself lucky, because that man…He is incredible. He is everything I could have hoped for in a son and more. _

_ When I look at you I see this strong, determined, and trustworthy person. A hero, who has fought for innocent people and who continues to strive for the betterment of the world. I see a man who protects his family with a ferocity these angels should fear. The way you always have one eye on Sam. I don't think you're aware of it. It's clearly second nature to you… But I notice and it makes me smile. And the way you work to protect me and John, even against all odds. Everything about you is honest (as a hunter can be) and loyal, and I couldn't be more proud of you for that. What mother wouldn't be proud to have a son as dedicated as you are to saving his family, friends, and even total strangers? No mother in her right mind, that's who… I am honestly impressed by you. Your mother is truly impressed by you Dean, so don't you ever forget it. _

_ So boys, I guess I wanted to say all of this to you in case I don't get that chance. I am so proud of both of you, and I need for you both to know it. Not many mothers get the chance I've been given. I get to see who my sons become after I'm gone. And I am telling you honestly that the grown men I've seen. My adult sons… They are men any mother would be showing off like a prize. You're heroes, both of you. You are kind, strong, intelligent, brave... You're both even handsome. I couldn't ask for more than you two, and I wouldn't change a thing about you, save the pain you've both had to endure. _

_I love you both so much, and I want you to remember that. Even if after this is over I don't remember having met you. _

_Love,_

_Your Mother_

**Secondary Author's Note: Thanks for reading! Reviews and requests are always awesome, so feel free to send 'em my way! **


	48. Useless

**Author's Note: This letter was requested a while ago by ClassyMuse, who said she wanted a letter from Dean to Endverse-Cas, because she loved that version of Castiel the most. Man, ****you all give me such awesomely challenging requests! **:D So here goes... I am going to say Dean wrote this (probably while kind of drunk) several days after he got back from 2014. I want to thank flygirl33, kingdommast, mb64, jojospn, ClassyMuse, WomanOfLetters, SPNxBookworm, judyann, reannablue, and GuestJ for their recent reviews and support. And thanks to all of you amazing readers!

**Disclaimer: I don't own _Supernatural_. **

_Cas,_

_ You know in all the times I've called you by that nickname, never has it fit you so well. I mean I started using it because I thought "Castiel" was just too stiff. So were you at the time, but I was hoping to kind of change that a little. Maybe help you relax around me and Sam. But seeing you all stoned and 'free love'… Well I guess I got you to relax a lot… _

_ But come on man. There's relaxed and then there's totally whacked out of your mind. And much as I never thought I'd say this, seeing you so whacked made me really miss Castiel. The guy who walks around like he's got a metal rod stuffed where the sun don't shine and always wears an expression of utter seriousness. Because you are many things dude, but you sure aren't him. _

_ So it makes me wonder just how much crap he had to go through to become you. Yeah, I know he became human. Fell, or whatever. But even that wouldn't have been enough to re-write his whole personality I don't think. No, there had to be more. I thought about this the whole time I was around you, and then it hit me. See, you mentioned that you broke your foot and were out of commission for two months. And you called yourself useless. _

_ And suddenly I understood. You bury yourself in drugs and women, not because you want to "bang a few gongs before the lights go out", but because you genuinely don't want to have to think about the fact that those lights are going out, and you can't do anything to stop it. Or so you think, because like you said, you feel useless. _

_ And I'm sorry man, because future-me should have been the person to tell you that's not true. But he was a dick-bag, because he apparently didn't care at all that you weren't so much falling from Heaven as much as you were just plain falling apart. I'm sure he gave you excuses like "I'm busy" or "there's too much on my mind already". What he should have said is "Hey, you're not useless." Simple as that. Even when your foot was broken he should have told you to haul your lazy ass onto some crutches and help him with something. It sounds harsh, but I think it would have made a difference. He should never have let you slip away like that. _

_ But I'm promising you right now that I won't. I'm already doing things differently by teaming up with Sammy again. But I swear that I'm going to look out for Castiel too. If he's destined to fall from Heaven, then so help me, I am going to be there to make damn sure he doesn't fall from humanity too. He's done too much for us, and if it's true that he's going to sacrifice his angel mojo by fighting on our side, I am going to give him better recompense than you got. If I have things my way, he will never end up that broken shell of a man I saw. He will never become you. _

_ Not that I think you're a bad person. Believe me, I didn't miss the fact that even after I had clearly been a neglectful friend, you still volunteered for a suicidal mission just to help me. I didn't deserve that kind of loyalty but you gave it anyway. Apparently, no matter how much of an ass I am, you'll still have my back… I don't know whether to be grateful or guilty. I guess I'm both. _

_ But hopefully I can change things enough to fix that future. I mean, I admit there's a good chance the world will still go to Hell around us, but at the very least I'm going to keep us all together. And I'll do my best to keep us, well…us. Sammy isn't going darkside, I'm not letting myself become your "fearless leader", and Castiel is going to stay as socially awkward and uncomfortable as ever. We're not changing, and we sure as hell aren't changing into that future. _

_ So thanks, Cas. I'm never going to see you again, but I want you to know I'm grateful I saw you in time to save you. To save us all from ourselves. _

_Dean _

**Secondary Author's Note: Thanks for reading! Reviews are still greatly appreciated! And as I am approaching letter number 50 (which is still a source of disbelief for me by the way), requests are especially welcome. :D **


	49. My Heaven

**Author's Note: This is a letter for kingdommast, who requested "A letter from Sam to Dean explaining why his favorite memories are of when he wasn't in the family business." I took it upon myself to focus specifically on his Heaven memories. Hope that's ok kingdommast! So here is a letter from Sam to Dean, written sometime shortly after their little trip to Heaven in season 5. I want to thank jojospn, kingdommast, mb64, ClassyMuse, shirleypositive72, judyann, SPNxBookworm, and Garideth for their recent amazing reviews. And thanks to all of you who read these! :D  
**

**Disclaimer: I don't own _Supernatural_. **

_Dean,_

_ I know you're upset that all the memories you saw in my Heaven were from times when I wasn't with the family. I know you're hurt because you gave everything to me over the years and it must have seemed as though none of that mattered to me. I also know you won't believe me when I say this, but it did matter._

_ You don't remember, do you? But that Thanksgiving you saw…It's the first real Thanksgiving I ever had, and you are the one who convinced dad to let me go to it. He didn't like Thanksgiving, so why should his boys? But you begged him on my behalf. Told him that it was a big deal to me, and that he shouldn't spoil the night for me. I remember you actually said, "It's not like he's asking you to cook. You don't have to do a darn thing except let some girl's parents feed him. It even saves you money." _

_ He finally caved, and I got to go spend three hours at that house feeling normal for once. And it meant a hell of a lot to me. It was awkward, yeah, because my date kept trying to grope me under the table… But it was still pretty fun. For once, I got to have a Thanksgiving where dad didn't drink himself into a stupor because he was depressed, and where you weren't forced to pretend everything was cheerful for my sake. Don't get me wrong. I always appreciated that you'd do that for me. But I thought you deserved to crumble every now and then too. I figured on that night, you'd get to have your moment of private reality to fall apart, and I would get to have my moment of fantasy to pretend things were fine. _

_ I guess looking back on things I should have known you probably liked having to put on a smile. That you didn't want to face reality because it hurt, and wearing a fake smile was better than the pain. But even so, you let me go that night. So thanks. _

_ And I know it pissed you off to see Flagstaff as a part of my Heaven too, but it's not there for the reason you think. I didn't run away because I wanted to abandon you and dad. Honestly Dean, I know it was there because that was the first time I got to prove to myself I could handle things on my own. Dad had always kept a pretty strict eye on me, and you had always had my back and protected me. And I was grateful for that…Still am. But for once, I got to feel independent. Yeah, I was living on old pizza and rooming with a stray dog… But it was worth it to feel strong. _

_ It wasn't that I didn't love my family, or that I wanted to leave them forever. I just wanted a chance to stand on my own two feet, if only for a little while. After all, I was supposed to be your backup on hunts. Yet I had never proven to myself I was capable of handling anything on my own. How could I watch your back if I couldn't even watch my own? After Flagstaff, I had proven to myself that I could take care of things. I finally had some faith in my own abilities. _

_ I guess it didn't occur to me how much trouble you would be in since I snuck off on your watch. Dad was massively pissed at you, and it was my fault. I am sorry about that, really. _

_ And then there was Stanford. I think that one meant so much to me because it was the start of a better future for me. I made a choice for myself that would help me actually live a life, and not just go day to day hoping something nasty didn't kill me. I do want you to know that, even though it was in my Heaven, it wasn't perfect. I swear, Dean, that the night I left I was actually kind of terrified. I knew I wanted to do it, but that didn't make it any less daunting. And I know you probably won't believe me, but I missed you from the moment I walked out the door until the moment you broke into my appartment. You're my brother and closest friend. No amount of miles or hours was going to make leaving you any easier.  
_

_ And I feel I should mention that you were wrong. When you said my whole Heaven was made up of my most perfect memories, which were all running away from my family? You weren't there for the memory I woke up to. When I first got there, I was standing by an old rail bridge talking to you. Like, modern you. And you were telling me that you still wanted to have me by your side if you were going to try and stop this apocalypse. You were letting me back in. It definitely wasn't perfect, because it felt more like Hell than Heaven to be reminded of how badly I had let you down in the first place... __But I can still understand why that memory is a part of my Heaven. _

_____They say Heaven is supposed to fill you with a sense of being unconditionally loved. Well, i_n that moment I was actually running back to my family. And my family... He still wanted to have me back. Even after everything I'd done. 

_Guess they're right about Heaven after all. _

_Sam _

**Secondary Author's Note: Thanks for reading! I have been loving the reviews and requests you guys give me, so feel free to keep throwing them at me! :D **


	50. Innocent

**Author's Note: So this is actually my 50th letter. I literally cannot believe I made it this far! I didn't want to try and do anything crazy for letter 50, because I didn't want to risk going overboard and ruining it. But I did want it to be a brothers letter, so here is what I decided upon: This is a letter from Dean to Sam, shortly after 2X14 "Born Under a Bad Sign". Dean is explaining to Sam why he wouldn't shoot him before he realized Meg was possessing him. I want to thank each and every one of you incredible people who has read these letters thus far. **** I love you all with so much love.** :D I also want to thank reannablue, SPNxBookworm, judyann, kingdommast, WomanOfLetters, and jojospn for their recent reviews and support.  


**Disclaimer:_ Supernatural_ isn't mine. But it definitely owns my soul. **

_Sammy,_

___While you were possessed that bitch had you put a gun in my hand and ask me to shoot you. It was right after we saw the footage of you offing that hunter. She had you tell me you knew it was out of your control, and you needed to be stopped. I didn't shoot, _because I knew it couldn't be you. By that I genuinely mean I know you, and you would never in a million years go around randomly killing hunters. Now before you get all pissy, allow me to explain my logic... 

_Remember the vampire case we worked a little while back? I was all gung-ho to kill them all, no questions asked. But you… You kept a level head and listened to the vampires. And because of that, you pulled me back from the edge of a really bad decision, and you saved a lot of innocent lives. And how did you do it? By being kind and compassionate. You were empathetic toward the vamps. Enough to where you could see beyond the nasty fangs to the decent people who were trying to live their lives without hurting anyone._

_ It was something I wasn't able to do. Hell, without you there I would have killed them all. I would have teamed up with freaking Gordon to do it, too. And it probably would have turned me down a pretty dark path. But you were there to stop me. You saved me from that and all because you're such a good person. Now tell me, how was I supposed to believe the guy who risked his neck for innocent vamps had turned around and started murdering people for fun? _

_ And that's just one example. Do you know how many times I can think of that you've been the poster-boy for good deeds? I mean, think of all the times you've charged full-speed into the line of fire to protect people from the evil things we hunt. I can think of so many of those moments... I couldn't count them even on ten hands. You know how many times the majority of the population can say they've done something good like that? Zero, in most cases. Sometimes one or two maximum. But you've got a list a mile long. What does that mean to you? Nothing, apparently, but I can tell you what it means to me… It means that there's no way in hell I could ever associate you with being evil.  
_

_ And I know what you'll say to me. You'll tell me that it doesn't matter that you aren't evil now because you're supposed to be changing into something evil eventually. You'll say that it's not you I have to watch out for, but whatever you're supposed to become. Well you know what? I don't buy it. I think all these psychic kids going darkside… They've got to have had it in them to begin with. People don't just flip like that. And you? You sure as hell don't have it in you. Not to mention you have more self-control than just about any person I've met. You eat salads instead of burgers, even after hours of foodless travel. You got straight A's all through school, and never slacked off on a single assignment, even in the middle of a hunt. You are basically the essence of self-dicipline. _

_You're the nicest, most controlled person I know. And I do know you. Better than I know anyone else. So hearing you tell me you had lost control of yourself completely and had turned into some kind of monster... I wasn't buying it. I knew that it couldn't be you. I knew you had to be innocent somehow. And h__ey, you're the one who taught me that killing innocent creatures just because they've been labeled as 'bad' is wrong. I didn't want to be wrong.  
_

___Although you might not have faith in yourself, I will always have faith in you. I hope you know I will do whatever it takes to protect you from whatever this whole thing is. You're my jumbo-sized little brother, and I'll never stop looking after you. ____I would give almost anything to help you. _  


_____________Except I wouldn't shoot you__, because that couldn't have been you._

_______________But mostly because I'd rather die, Sammy. _

_Dean_

_P.S. If you need more proof that you couldn't possibly turn evil... Name me one seriously evil being who was petrified of clowns. Can't think of a single one, can you? I think I've made my point.  
_

**Secondary Author's note: ****I really don't have words to express my gratitude to all of you adequately. I think I'll invent one: I am so grateful, I feel Fantabulon!** :D **Seriously, you've all been so amazing and I really can't thank you enough. ** I also want to make clear that I am still going to keep this series going, so requests and reviews are definitely still welcome! :)  



	51. Parallels

**Author's Note: So this letter is for SPNxBookworm, who recently requested "A letter from Charlie to Dean a few days after she snaps out of her djinn induced dream." Well here it is! A letter from Charlie to Dean after 8X20 "Pac Man Fever". I want to thank mb64, jojospn, kingdommast, reannablue, judyann, Angie, and Garideth for their recent awesome reviews. And thanks to all you wonderful readers! By the way, I hit over 10,000 views recently. WOW! I am so grateful. :D **

**Disclaimer: I don't own _Supernatural_. **

_Dean,_

_ I know I already sent you and your brother a letter thanking you for saving me, and being there for me, and all of that good stuff. But I felt like I should probably talk to you more about that whole dream world thing you saved me from, and I'm kinda betting you don't want Sam reading what I have to say. So for the sake of helping save you from Sam's sensitivity and brotherly concern, I am writing you your very own letter. You should feel so much gratitude right now…_

_ Anyway, I was thinking over what you said to me in the dream world. About letting go and accepting that I couldn't save my mom? It wasn't easy to do it you know. In fact that was probably the hardest decision I've ever had to make. And as you know, I've made some pretty hard decisions. *cough* Sneaking into Dick Roman's office to save the day for you and Sam. *cough*. But this choice was harder, for many reasons…_

_ First, she's my mother. I know it sounds cliché and all, but I love my mom more than probably anybody else. Why do you think I risked my backside consistently with all the illegal fund transfers and what-not? Did you seriously think it was just because I liked proving I could steal money from the 1%? Ok, so I guess that WAS part of it. Still is, too. (What? It's hard to not want to use my genius to pull a Robin Hood and take from the rich to give to the needy...) But I wouldn't have done it so often if the "needy" hadn't been in quite as much need. _

_ My mother needed me because she would die if I didn't keep buying her more time, literally, to stay in that hospital on life-support. But that was all I could do to help. Buy her time to lay there. And it was killing me inside to think I couldn't actually fix everything for her. That I couldn't save someone I loved so much... _

_ But it was also because I felt responsible. I told you why already. I got scared at some stupid pajama party and made my parents come get me. I stranded them in the car that night on the road that would lead to their deaths. Only my mom didn't die right away. She stayed in a coma and clung on somehow. She was always tough like that. But even so, she would never be the same again. I would never again have her there to tuck me in, or read me adventurous bedtime stories, or to just sit with me and make me feel better when I was upset. I would never have my mother back, and it was my fault. I screwed up and she suffered. _

_ I guess it felt for the longest time like keeping her alive was my way of trying to apologize. Of trying to make up for having let her down. If I could just keep her going, then maybe somehow she would know I was sorry. She would understand that I had never meant to hurt her, and that I would give just about anything to protect her from everything bad that happened to her…_

_ But in the end you were right. I was keeping her here because I needed to. Because I wasn't sure what I'd do without her. But she wasn't really living. And when you finally made me realize that I needed to let her go, it hurt. It hurt because I saw how long I'd been forcing her to stay here because I needed her around, and I also saw just how long it had been since really was, well, around. But I also remembered how she was before the accident, and I realized she would never want this for me. For me to hurt and blame myself all the time. She would want for me to let her go, and so I did. Like I said, it was a really hard decision. It hurt and I cried. But in the end, I got through it. And you helped me, so thanks again.  
_

_ But I'm not saying all of this because it's therapeutic for me to share my feelings with someone, or because I felt like killing a tree to write you a story you already know for the most part. I wrote you this letter so you could look at my story on paper, and maybe draw the parallels I see between your situation and mine. I mentioned it before when I was leaving your (totally awesomesauce) bunker… I asked if you were ready to let go of what you were holding onto. _

_I saw Sam lying in that hospital bed in the dream world. I saw you hesitate to put your weapon down because you were scared you would get him killed. More importantly, I still see the way you hover over him the whole time he's in the room. Always watching and always concerned. Always looking like you're ready for him to drop, but like you'll probably lose your mind if he does. He's what you can't let go of. Now please don't misunderstand. I'm not asking you to stop caring if Sam lives or dies. I've read those Supernatural books and believe me, I know you will never do that…Nor should you. _

_ But I am saying that I can see you love him more than anyone. And I know you blame yourself for everything that's happened to him. For everything that is still happening to him. I know you've been doing everything in your power to protect him practically since he was born, and yet you hate yourself for not being able to save him from the stuff he's dealing with. You're upset that you can only do your best to keep him alive, but you can't necessarily save him. _

_ Seeing the parallels yet? I'm not telling you to let him go as in let him die. Like I mentioned in that letter I sent before…I have full confidence that he'll pull through this one. And I know that no matter what I say, you'll do everything you can to help him with that. Which is probably for the best. Harry would never have been able to do any of the stuff he did without Ron and (mostly) Hermione backing him up. And you had better get that reference or I swear that I'll disown you. _

_ Basically, I'm telling you to take some of your own advice. Let go, not of Sam himself, but of all the self-loathing you keep subjecting yourself to over not having saved him from everything that's happened to him. It isn't really your fault. Because you would never have wanted him to have to deal with any of this. And I bet if you think about it like I thought about my mom, you'll come to a conclusion similar to mine. _

_Sam doesn't want you to beat yourself up constantly because you couldn't protect him from every bad thing in the world. He wants you to be happy, just as much as you want that for him. And if I know you like I know the Dean in those books (Not trying to creep you out, I promise) then I know you would do anything for Sam. Even something as hard for you as letting go and forgiving yourself. _

_Charlie_

_P.S. I am guessing the realization is setting in that I really could have chosen to write all of this in that first letter. And then Sam would've read it, and he would have used his patented puppy-dog eyes on you until you caved and had to the brotherly heart-to-heart thing… Consider the fact that I didn't put you through that my way of repaying you for the whole saving my life thing.  
_

**Secondary Author's Note: Thanks for reading! Reviews and requests are definitely still welcome. :)  
**


	52. Good Times

**Author's Note: This letter is for mb64, who recently requested "Maybe you could just do a happy (no angst at all!) letter from either Sam or Dean to his brother remembering some happy times together? (shooting the fireworks, the thrown together Christmas before Dean went to hell, and a few that we don't know about?)" I loved this request, and I hope I did it justice. :) I want to thank judyann, mb64, jojospn, SPNxBookworm, flygirl33, WomanOfLetters, and GuestJ for their recent awesome reviews. And thanks to all of you great readers!  
**

**Disclaimer: I don't own _Supernatural_. **

_Dean_

_So do you remember when I told you I was recalling things from my life in extreme detail? I'm pretty sure you do, because it was around the time I was ranting about when you rode that gassy donkey… Anyway, at first it was freaking me out having such a clear memory of all these tiny moments in my life. But then I started to enjoy it. I mean there are a ton of good memories that I hadn't thought about in so long... _

_Like that Fourth of July back in 1996. You took me out to that field in the middle of the night to light up our own fireworks. And I remember it was stormy that night, and it smelled like wet grass in the field. That is until we lit those first two fireworks together. Then there was this amazing smell of gunpowder and rain. I remember looking up at you and telling you that you were great for letting me do something like that, because dad would never have approved had he been awake when we snuck out. _

_And you looked down at me with this expression that was so intense, but in a good way…It was like you were on top of the world. I gave you a hug and you laughed about how girly I was being, but it was one of those times where I knew you were actually ok with the 'girlyness'. And then you looked at our crate of explosives and gave me a nod like you were telling me I could do whatever I wanted with them. _

_So I took your lighter, that old zippo you got as a gift from dad when you turned 15, and I lit basically every firework in the crate. I'd never actually lit a firework before that night so I was kind of nervous as I watched the wicks burn. And they all went off at once and there was so much light! And I remember thinking later on that we were lucky the grass was so damp, or else we'd have probably lit the whole field on fire._

_But in that particular moment I wasn't thinking about safety at all. I ran out to the center of the shower of sparks and jumped around, just staring up at all the colors and grinning. And you were looking on with actual pride, as if nothing in the world could have satisfied you more than for me to be there dancing in the middle of a random field under the remnants of one hundred dollars' worth of holiday explosives. And in that moment, everything was perfect to me. _

_And then there was the Christmas we had about five years ago… I know it was tense at the time, what with you being sentenced to Hell and all that. I also know it seems weird that I'd be so happy to remember it, because I was the one who kept trying to avoid celebrating that year. But I look back on it now and I love it. Partly because it was very, I don't know…Us? I mean we had a tree decorated with freaking air freshener and fishing lures. It was the epitome of us. But I also love it because I look back on that day and remember the way you didn't want to give up what you thought would be your last chance to sit around a tree with me drinking eggnog and watching sports._

_And when you walked into the motel room and saw I'd decorated, you looked…well you looked touched Dean. Not in a dramatic movie scene way, but like you were just happy to see I had caved. You asked me what changed my mind and I didn't exactly give you an answer back then. Well I can say to you now, honestly, it was the realization of why you had tried so hard to convince me to celebrate with you. That it wasn't because you wanted to have a last holiday, but because you wanted to have a last holiday with me. How could I really say no to that? And so I made sure I was there for you, and that we celebrated. Because if the tables had been turned I knew I would've wanted a last holiday with you too. And you would have given it to me, because you've always done anything you could to make me happy. _

_For example, do you remember when I was six and I had you take me camping? Well not actually outside, but we definitely made a camp … I remember I had asked you what it was like to go camping because I had heard some people talking about it on a TV show. You told me it was when people slept outside without a bed under a roof made of cloth, and that it was really dirty. I think you assumed I wouldn't find that to be appealing. Instead, I started begging you to take me camping. And after two hours of not succeeding in convincing me that you couldn't do that, you gave in and told me we'd find a way to camp in the motel._

_So you took the chairs from next to the little table and put one on each of the twin beds. And then you tied all the blankets and sheets in the whole room together into one giant cover that we draped over the chairs and beds and everything in between. We turned the lamp on that was on the nightstand between the beds, and then shut all the blinds and turned off all the other lights. And we had this glowing little cave thing made of bedding to hang out in. We sat on the floor between the beds, and you said "See Sammy, we're basically camping now. We're not on the beds, we're under cloth, and this floor is really dirty." I took that so seriously at the time. And then I made you sleep in the "tent" next to me that night. _

_I was also thinking recently about the day you taught me to swim. Do you remember that one? I was four years old and we were staying at a motel with a pool for once. And dad was doing his research by the poolside so we could have a break to cool off. I was splashing around the shallow end, but then you went over to the deeper part and I remember thinking I would give just about anything to be able to follow you there. So I tried to. And of course I immediately started to sink. I got scared and started thrashing around, but before I could even fully dip under the water once, you were there holding me up. And you were of course totally freaked out that I had, as you put it, "almost died". Two seconds of me struggling and it got classified as a near death experience. And you say I'm the dramatic one Dean…_

_Anyway, suddenly our little play time in the pool was a serious swimming lesson. It was obvious you had decided you should teach me to really swim before I drowned someday. So you started teaching me how to use my arms and legs to dog paddle, and then how to keep my head above the water, and eventually you showed me how to full on swim. After hours of you working with me on "prefect technique", I got to go with you to the deeper side. Which in retrospect was really pretty shallow. It was only four feet deep, so it would be like stepping in a puddle for me now. But back then? Man, that was the biggest achievement of my life! I mean, you totally hovered next to me the whole time ready to grab me if I messed up. But I still felt like I had just conquered the world. And you had helped get me there._

_I know these memories appear so small compared to the mountain of stuff we've been through in our lives. But somehow… I don't know Dean. It's like remembering these little events as though they happened just yesterday… It's amazing. It makes me see how many parts of my life have been really good. Hell, most of these memories even make me feel sort of normal. Like I did have moments where I was just an average kid growing up with his big brother. So I guess they might seem small to an outsider, but they're like a collection of every time we've gotten to just be brothers, and that's huge to me. My own collection of all the good times. So thanks, I guess. For giving me so many good memories to want to hang onto. _

_Sam_

**Secondary Author's Note: Thanks for reading! I've been getting some really good requests, and I'm loving it. Do feel free to keep them coming! Also, reviews are incredibly appreciated. :D  
**


	53. A Lot Of Them

**Author's Note: So this letter was written to fulfill multiple requests. After the last letter, jojospn and kingdommast both requested a response letter from Dean. Also, SPNxBookworm asked for a similar letter in which Dean tells Sam some of his favorite memories. Finally, mb64 requested an angst free letter from Dean to Sam, like the way Sam's letter to Dean had been. Well, here it is! My attempt at combining all of those requests into one angst-free, memory-filled, response letter from Dean to Sam. I want to thank judyann, jojospn, shirleypositive72, kingdommast, SPNxBookworm, mb64, the Guest "TG", kjdw, flygirl33, ClassyMuse, lilliannaelizabeth, GuestJ, WomanOfLetters, and reannablue for their recent reviews. And a huge thank you to everyone who reads these! :D **

**Disclaimer: I don't own _Supernatural_. **

_Sam,_

_ Wow, you really are remembering a lot aren't you? I had completely forgotten about the night of the motel tent… Looking back on it, yeah, you were so happy about that. I guess you were a pretty easy kid to please. Give you a bunch of tied-together old motel sheets covering a crawlspace between some rickety beds and you might as well have been in Disneyland. _

_ And I hadn't thought about your first swimming lesson in a while either. First and last lesson, actually. You must've learned to swim faster than any kid in history! One minute you were in danger of drowning, and a few hours later you're swimming around like a pro. Of course you learned to walk that fast too. You're just a quick learner, I suppose. And yes, I freaked out when you DID almost drown. You were sinking, and you couldn't swim. That's called drowning, Sam. And if I had allowed you to finish drowning, you would have died. I was not being overly dramatic, I was saving your life. Oh, the ingratitude… _

_ I do remember that Fourth of July you were talking about though. I remember it perfectly because it was the thing I woke up to when we went to Heaven. But it was cool to get a look at it from your point of view. And I was definitely glad to hear it's as good a memory for you as it is for me, because I paid a lot of money for those fireworks. Goodness knows dad wouldn't have bought those for us in a million years! But it was worth it. It was definitely worth it. _

_ And that Christmas… Man, reading about that one got me. I remember it fondly too. And even though I made it back from Hell in time to have technically not missed any Christmases with you, that one always stands out to me. Probably in part because we still don't really celebrate Christmas except if one of us is sentenced to die before the next one, and luckily that hasn't been the case since then. But mostly because that Christmas you were willing to suffer through the emotional trauma of it to give me "one last holiday with you". And it meant more to me than the motor oil and protein bar you gave me ever could, although I'm not knocking those gifts. They were perfect. That day was perfect. Or, well, as perfect as it could get what with the Hell-sized elephant in the room with us. But it was great, really, so thanks for reminding me of it. _

_ Geez, now you've got me going full on chick-flick… But I guess it's, how did you put it? "One of those times where I'm ok with the girliness"? Yeah, I suppose I am. I mean, I haven't exactly had a chance to go over all the good times in my mind lately. And it's surprisingly therapeutic. Hey, what do say I share some of mine with you? Good memories of us, I mean… _

_ Like that time when you wanted to ask out that girl from your 7__th__ grade class! Suzie Something-or-other. I'm bad with names… Anyway she was cute, and you definitely thought so. And you came back to the motel after school looking all flustered, and I asked you what was wrong, and you just looked and me and said, "It finally happened. I finally like a girl." You looked really torn up about it, and I was like, "You say it like you've been dreading it…Why is it bad, Sammy?" And you sighed like I was being a total short-bus and told me, "Because I don't know what to do. I don't know how to talk to her, let alone how to ask her out. And If I do ask her out, it's not like I can stay in town long enough to actually date her." _

_ I admit it kind of threw me, because I had never personally been the type to want to get attached to a random chick anyway. But I knew you, and knew you were the caring type. So I told you that it was ok to just take a girl out on a date, and that it didn't have to mean forever. I told you it was the perk of being young. You date for fun, not marriage. But you get the experience you need so that one day you'll be ready to find the right girl to actually settle down with. That seemed to cheer you up, and then we spent the next hour planning strategies for how you could ask her out. _

_ You asked her out the very next day, and she said yes. I would never have said this to you at the time, but I knew she would. I mean, your trademark Winchester good-looks and your trade-mark Sammy eyes were like a lethal combo. No way was she going to say no. And so you guys went out a couple times during the month we stayed at that motel, and you were so happy for that month. _

_ And then the day came when we had to move on. You did look sad, but then you did something I was really proud of you for doing. You called her up, and let her know you were leaving town. You said your goodbyes and ended it on good terms with her. It was something I never did because I was always bad at goodbyes. Scared of them, I guess. But you handled it like a gentleman, and when the phone call was over, you looked at me and thanked me. For having convinced you to go for it despite the fact that it wouldn't last. You told me you'd had fun with her and that it had been worth it. It put me on top of the world knowing I had helped you get over your fear of dating. Made me feel like I had successfully done my big-brotherly duty. _

_ Oh, and on a totally different note… Do you remember my 15__th__ birthday? That was the year dad dropped us off at Bobby's while he went hunting, and you decided to throw me a party. And at eleven years old, you got on the phone with all of dad's friends and convinced them to drive up to Bobby's to surprise me. And because you are so gifted with the art of persuasion, they actually did. Caleb, and Pastor Jim, and a handful of others… They all showed up and brought presents and pie. And it was great. I felt like I was a part of a giant family for once, even though every member of that family was messed up in their own way… Still. It was perfect. _

_ And when it was over and they had all left and Bobby had gone off to bed, you and I sat on his porch just talking. And I asked you what had inspired you to put so much effort into this birthday, and you just looked at me and said, "Why not? You always put effort into mine." You said it like it was nothing, but to me it was everything. _

_ God, I am getting girly here, aren't I? I better stop while I still have a pair. Anyway, I guess I just want to say thanks for getting me to think of all this stuff. It is nice to reminisce the good times occasionally. And thinking back on everything, I guess we've had a lot of them. _

_Dean_

**Secondary Author's Note: Thanks for reading! Reviews and requests are incredibly welcome. :D **


	54. Efforts

**Author's Note: This letter is for Leia 96 who requested a while ago a letter "from Amelia to Dean, even though she never met him, about how Sam's dealing with his 'death.'" This was a very interesting suggestion, and I knew I had to do it. :) So here it is, a letter from Amelia (season 8) to "dead" Dean. Before you read though, I must clarify a couple things. 1) Amelia knows nothing about hunting, monsters, or any of that. I try to keep these letters cannon, and Sam never told her about his real history in the show. So if it sounds like she knows anything about it, she doesn't. It's coincidental. And 2) I personally never cared for the character of Amelia on the show. However, I tried to write this from an unbiased perspective. And if you liked the character of Amelia that's great. To each their own, I really don't judge. :) I want to thank judyann, kingdommast, jojospn, ClassyMuse, GuestJ, shirleypositive72, reannablue, mb64, SPNxBookworm, and flygirl33 for their recent amazing reviews. And thanks to every one of you who reads these! **

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ My name is Amelia. You don't know me at all, but feel like I know you thanks to your brother. I'm Sam's girlfriend, and I don't really know why I'm writing this to you. I think because I felt the need to talk to someone who I know cares about Sam as much as I do. He…Well I don't want to say he's not doing well. He is doing fine most of the time. Or so it appears. But underneath the casual exterior I know he's practically broken. It's hard to explain. One minute we'll be taking a walk and just chatting, and the next he'll be staring off into space with this intense look on his face. Like he's in pain. And then I'll notice what he's actually looking at, and I'll know why he's hurting. But I won't always know how to help. _

_ See, at first I didn't even know what was causing those moments. It took me a while to understand because I couldn't connect the dots. Like the first few times it happened, it was something that appeared entirely random to me that set him off. One time we were in a toy store buying a present for my friend's kid, and he saw these little plastic army men and went dead silent, just staring at them for the longest time. I figured they meant something to him, but I had no idea what. _

_ And then another time we were at the hospital to visit my dad who had just got his appendix removed pretty late in the game. And then suddenly this teenage guy on a gurney got rushed past us in the hall. He was covered in blood and the nurses and everyone were calling things out. I heard someone say "animal attack" as they ran past. When they were gone I turned to look at Sam and I saw he was sheet white and his fists were clenched. He actually had to go off on his own to regain his composure. And I couldn't follow him to offer comfort because I had no clue where to even begin…No idea what was wrong. _

_ But eventually came the time when I actually figured it out. We were sitting at our favorite spot in the park with our dog, just enjoying the mild weather… And we were watching some kids across the field play soccer. One of the kids shoved a smaller boy out of his way as he ran for the ball, and the smaller boy fell over. Immediately, a bigger boy came running to the little one's side, all concerned. The little kid must've been fine because the bigger boy quickly turned his attention to the kid that had shoved him. And even from where Sam and I were sitting we could hear the bigger boy clear as day tell the kid who'd shoved the small boy to "Never friggin' touch my little brother again you ass."_

_ It was certainly colorful language to be coming from a kid who couldn't have been more than eleven. But I somehow didn't think that seeing a kid cursing was the reason Sam was tearing up and had to look away from me. It suddenly clicked, and I felt so stupid for having missed it all along. Especially because Sam had talked to me about the fact that he lost you. All these moments where he kept freezing up, looking like he'd seen a ghost…In a way he had. _

_ He had seen something that reminded him of you. That had brought up memories that were like little pieces of you still floating around. Over time I got him to fill me in on reasons for things. Like the next time it happened, he had seen someone at a restaurant eating a piece of apple pie like it was the love of their life… And he looked really pained for a moment, so I asked him to talk about it. And thankfully he did. He told me all about your obsession with that particular baked good, and he even smiled a little about it once I got him talking. And ever since then I've managed to convince him to talk more about things. To tell me more about you. And he seemed genuinely pleased after a while to share stories of the two of you. _

_ But I still worry, because there are so many moments still when he won't open up. So many times when he gets that distant look and I can't get him to talk about why. I can't pull him back from the pain. And I wish with all my heart that I could. It's like there are some memories he's just not ready to share with me. And sometimes I wonder if they're memories he wishes he could forget. The haunted look he gets, like that day in the hospital…It's unnerving. _

_ But I know he doesn't really want to forget. If there's one thing I have learned after hearing all the things he's shared with me about you, it's that you meant the world to him. It couldn't be more obvious. I don't know if a little brother has ever looked up to a big brother more… I mean the way his eyes light up whenever he remembers a particularly happy event with you. He loved you immensely, and I know he still does. _

_ I just wish I could help him more to deal with those moments when it hurts too much to talk about. I wish I could be the help to him that I know you always were. But hey, if everything I hear about you is true then maybe even in death you'll find a way to help Sam. I mean the way he talks about you? I believe that at the very least you'd try. That you would give it your all. And just hearing about all the times you took care of him inspires me to do my best to look after him now. I know I've got big shoes to fill, but I assure you I'm really trying. So here's to both our efforts. I know you'd agree it's definitely worth it. _

_Amelia _

**Secondary Author's Note: Thanks for reading! Reviews and requests make my day. :D **


	55. You

**Author's Note: So this letter is for WomanOfLetters, who suggested a letter from Lisa to Dean. I decided to put my own spin on that. I hope you don't mind! This letter is from Lisa to Dean, written sometime after Castiel wiped Lisa and Ben's memories. I want to thank shirleypositive72, Leia 96, mb64, judyann, GuestJ, flygirl33, jojospn, reannablue, and SPNxBookworm for their recent awesome reviews. And thanks to all of you who read these!**

**Disclaimer: I don't own Supernatural. **

_You,_

_ I know you. I look at your picture and I swear that I know you. Except I really don't, because I could also swear that I've never seen you before in my life. But I must have because in that picture you are sitting there with Ben and I at our Thanksgiving table. And it's just the three of us, as far as I can tell. Three plates at the table, portions too small to serve a ton of others…Not to mention your arm is angled upward so I know you were holding the camera, not somebody else. So tell me, how is it that I could have invited you over for Thanksgiving to share it alone with my son and I, and yet I can't remember a thing about you?_

_ Well that's not completely true. Looking at your face…I feel this incredible pull when I look right into your eyes. And pain, too. Though I can't tell if the pain is my own, or sympathy for the pain hiding under your smile. I see hurt in those shockingly green eyes. I see suffering behind your cheerful exterior. And I feel this desire to reach out to you. To comfort you and to wrap my arms around you and tell you it will all be ok… And as I feel this, I remember that you weren't ok. It's like I know you were so full of some kind of trauma. So lost and broken. _

_ But I don't even remember you, so how can I remember this? I can't even recall your name, and I can't honestly place a single moment in my life when I've seen you outside of the countless hours I've spent staring at this photo... _

_ I tried piecing it together. You know, figuring out when it was taken? And I eventually I narrowed it down to Thanksgiving of 2009. In the photo Ben is wearing a sweater he got for Christmas in 2008, and then lost a little over a year afterwards. And then I thought to myself, "Ok. So think back on that Thanksgiving…" And the damndest thing happened. I remembered spending it with my parents. I remembered driving Ben to my parent's house, and cooking in the kitchen with my mother. I remembered my dad watching the parade with Ben in the living room, laughing at the never ending string of colorfully dressed marching band members. But I sure didn't remember you._

_ I wasn't even at my house that year, and yet in this picture, that's exactly where I was. I almost called my mother to ask her if she remembered me being at her house, but then I stopped. Because what if I wasn't with my parents that year? What if I really was at my house, sharing the holiday with Ben and you. Wouldn't that make me crazy? Wouldn't that mean I was losing my memory? Or at least severely confusing it… I don't know what to think anymore. Ever since I pulled that picture out from under the fridge… Ever since I looked into your paper eyes and knew you without knowing a damn thing about you… Ever since I looked at you and wanted to help you but didn't know with what. _

_ I hate to admit it to myself, but I think I did know you. That maybe I am crazy or am losing my memory somehow. Because the feelings I get when I look at you…I don't even know your name, but when I look at you I feel... I feel the things that you must have been to me. I feel like rock music and old cars and whiskey. Like comfort and a promise of safety. But I also feel like fear and loss and hurt. Like a life so incredibly full and yet so impossibly empty. It's maddening, really. _

_ I guess I should thank you though. Because Ben and I…We look pretty happy in the picture. We are smiling these bright smiles. And not the fake ones that I see in most of my obligatory family photographs. No, they're real. We seem genuinely happy sitting there with a slightly burnt turkey, some mismatched dishes, and you. So thank you. But still…_

_ Who the hell are you? And why do you make me feel like crying and smiling at the same time? Did I lose you? Did I know you and then you died? I have too many questions that I'm sure will never be answered... Because I swear it feels like you were ripped from my life in a way so permanent it physically hurts. I'm sorry, but I think I'm going to burn this picture. I just can't handle it anymore. Can't handle seeing you and missing you, and something too painfully close to loving you. And yet not knowing at all who you are. I'm sorry. _

_Lisa  
_

**Secondary Author's Note: Thanks for reading! I absolutely love requests, and reviews are of course always appreciated. :D **


	56. More Important Stuff

**Author's Note: This letter came from the recesses of my own mind. It is a letter from Sam to Dean written while Dean was in a coma during 2X01 "In My Time Of Dying". Just something that I wanted to explore for fun. :) I want to thank kingdommast, mb64, jojospn, shirleypositive72, judyann, WomanOfLetters, reannablue, SPNxBookworm, and GuestJ for their recent reviews. :And thanks to all of you great readers!**

_Dean,_

_ I had Bobby tow the Impala to his place for you. You're going to want to cry when you see her, I'm warning you now… But I made Bobby swear he wouldn't junk her. She is a complete mess but I don't think she's beyond repair, and I'm not giving up on her. After all, you'd kill me if I did right? But while I was there dad asked me to get a list of stuff from Bobby. And you know what was on the freaking list? Stuff to summon a damn demon. He's actually going to try and summon the thing, in the middle of everything that's happening right now. _

_ You have to get back to us Dean. Dad and I are going to be the death of each other if you don't… I know you'd say that I'm just fighting with him for the sake of fighting because that's what I always do with him. But this time it's different Dean. Because this is you I'm fighting over. You've given us everything. Given this whole family your all, and yet dad is still more focused on the freaking demon, even when you're laying here and the doctors think that you're…_

_ I'm not even going to write it, because you're not dying. I'm not letting that happen. You're not even staying in a coma either. I'm going to do everything in my power to fix this because I owe you that much. You have always valued family above all else. And you showed me how to do the same. You stopped me from letting my desire for revenge push me to shoot my own father. Sure, dad had genuinely wanted me to do that… But I wouldn't have been able to forgive myself. He's my father, and I would've regretted that forever. But you saved me from that lifetime of regret. _

_ Well that's not really a shocker. I mean you've done nothing but save me for everything bad my whole life… You know I wasn't actually surprised to hear you'd been the one to carry me out of our house the night mom died? It was weird because I had never known that before, but at the same time it felt like something I should've guessed already. Who else would have dragged me out of harm's way? Even though you were only a toddler then, I still couldn't really imagine it being anybody else. _

_ And you never stopped carrying me away from trouble, did you? Yeah, you technically pulled me back into hunting. But God knows there isn't a person on this Earth I could rely on more to have my back on a hunt. Not to mention that I'm probably safer on a hunt with you than I would be on my own in some college dorm. Seriously. Every single time something nasty has had it out for me, you've made it your personal mission to ensure that thing dies bloody. And you've never once failed to do so. _

_ But now you're lying here hooked up to all these machines…And I think it's my turn to help you. I just wish I knew how. I keep begging dad to help, and he keeps swearing he will, but all he does is nothing. Unless you count developing strategies to confront the demon. If you count that then he's been busy as hell. But I don't count that. And I don't give a damn if that demon shows up and offers his head to me on a plate. I'm not paying him any attention at all until you're ok. Not until I've saved you. Because that last thing that bastard deserves it to take my focus away from you when you need it so much. _

_ Before the crash dad was telling me this demon was more important than anything. I told him it wasn't. Now dad's out there trying to find ways to hunt the thing, and I'm sitting here in your room reading his journal a thousand times over trying to find some way to help you. Guess we have our priorities in a slightly differ order._

_ I'm going to save you Dean. I have to. So just...enjoy the rest, I suppose. Because I know the minute you're back on your feet you'll be all over yellow eyes. And I promise that I'll be ready to fight him then too, right with you. Because I'll have gotten the more important stuff sorted out already. Because at that point you'll be ok. _

_Sam_

**Secondary Author's Note: Thanks for reading! Reviews and requests are definitely welcome. I was merely taking a brief break from requests with this one while my brain works out the kinks in some of the inspiration it got from recent requests. :) **


	57. The Right Choice

**Author's Note: So after the last letter (number 56, "More Important Stuff") I got two separate requests, one from LoveIsAllYouNeed96 and one from GuestJ, for a response letter from Dean. Because the last letter was written by Sam while Dean was in a coma, floating around basically as a spirit, I couldn't find a way to have the response written during that time period. So instead I chose to for Dean's response letter to be written after Dean finds the letter years later in Sam's junk. This letter was written by Dean some time shortly after 5X18 "Point of No Return", (The episode when Dean was getting ready to say 'yes' to Zachariah and Michael, but then didn't.) I want to thank jojospn, mb64, judyann, reannablue, SPNxBookworm, and GuestJ for their recent awesome reviews. And thanks to all you fantastic readers! :)  
**

**Disclaimer: I don't own Supernatural. **

_Sam,_

_ I was going through your bag today and I found something interesting. And before you get pissed, you ASKED me to go through your bag to find that book, remember? It wasn't like I was expecting to find a letter to me from years ago. But hey, it had my name on it! How was I not supposed to be curious? So of course I read it. And while I kind feel like I'm invading your privacy by even responding to the thing, I also feel like I have to. I mean the things you said… Give a guy a medal for being a total sap, but they were really nice Sammy. Especially considering we've been through so much since then. _

_ The way you were talking in the letter about dad. I miss the man Sam, I really do. And I feel awful knowing you were so pissed at him over the demon thing, thinking he was trying to fight it. I understand where you were coming from, don't get me wrong… But knowing what we do now, that in reality he was only doing what he could to save me… It hurts to remember that. _

_ But to hear the way you defended me? That you swore you wouldn't even look at yellow-eyes until you'd found a way to fix me up… I mean you wouldn't even admit I was dying, even though we both know that's exactly what was happening. Even privately written on a paper, you wouldn't say it. I've got to thank you for that. I've got to appreciate that you weren't ready to let me go without a fight. _

_ And you talked about being happy I convinced you not to shoot dad. That I "saved you from a life of regret". You know, I can remember even now how damned relieved I was when you didn't kill him. That you saw family should come first. I'm glad to hear now you were happy with that choice too. You were right when you said some things are just more important. _

_ And then you went on to mention the night of the fire. How you didn't know for so long that I'd been the one to carry you out of the house. You said it didn't surprise you when you learned that because I've always done my best to "drag you out of harm's way". Well I've done a bang up job with that lately, haven't I? I dragged you right up to freaking Zachariah, and he almost made you cough up your lungs on his too-clean marble floor. All so I could let you down by saying yes…_

_ Except I didn't. I didn't say yes. In that last moment when I was genuinely about to go through with it I saw you laying there looking up at me with your damn puppy eyes. It was like you were begging me not to say yes, but also accepting that I was going to. You looked so freaking hurt, but mostly just sad. Like you were just tired and kind of depressed that after everything we'd been through it would all end like that. But you weren't mad. I couldn't see even a hint of anger at me in your eyes. And in the end that's what stopped me. _

_ That even when I had been a dick to you and had flat out warned you that I was planning on giving up the fight I had pulled you into… You weren't pissed. You were just, I don't know. Sad to see me go? And I couldn't bring myself to do that to you. To make you watch me drop the ball after you had brought me there because you'd had so much faith that I couldn't actually let you down. I wasn't going to be another thing you'd put your faith in that turned around and crushed you. I mean, I remember how hurt you were when you realized what a bunch of asshats the angels really were... _

_ And now seeing this letter? It's like it proves to me I made the right choice. It reinforces all the reasons I couldn't do that to you. Because you've never given up when I needed you. Yeah, you've made a shit ton of mistakes…Haven't we all? But you have never just chosen to screw the pooch when I was in need. Apparently even when I was lying in a coma and you'd been told by medical professionals that I was dying. You just wouldn't give up. _

_ So I'm returning the favor I guess. I'm going to keep going and we're going to keep fighting this thing together. It's what we do. After all, we've got "more important stuff" to worry about than whether or not Lucifer and Michael get to wear us to their dance-off. We've got each other's backs to look out for. _

_Dean _

**Secondary Author's Note: Thanks for reading! Reviews and requests are totally amazing. :D **


	58. Familiar Face

**Author's Note: So this letter is part one of a a two part request I'm fulfilling. The lovely reannablue requested that I write "letters back and forth telling each other about things they did in their years apart while Sam was in college. I would prefer stuff that never came up in the series. Maybe Sam did participate in some crazy college antics before he met Jess?" Well, here goes. This is part one, a letter from Dean to Sam. I hope you enjoy! I want to thank LoveIsAllYouNeed96, mb64, reannablue, judyann, SPNxBookworm, jojospn, and a Guest for their recent reviews and support. And thanks to everyone who reads these!**

**Disclaimer: I don't own Supernatural. **

_Sammy,_

_ So you got A's on another round of midterms, huh? I'm impressed. Honestly, I'm not even being sarcastic. God knows I can't imagine the horrors of all those hours you must've spent studying for that. You deserve a bunch of A's for you efforts. I'm proud of you for keeping up the good work. If you do plan on staying out of the life for school, you should at least do your best to keep your grades up. And you're doing that, so good for you. _

_ I wanted to tell you about this girl I met the other night. And before you start your teasing, yes, I did meet her at a bar. But come on Sammy, where else am I going to meet a girl? A freaking library? Actually, that's probably where you go to pick up chicks, isn't it? I can just imagine you pouring over a pile of text books, glancing over at some smart chick all shy-like before hiding behind the pile again. You always were a nervous wreck whenever it came to girls. _

_ But I digress… Anyway, this girl I met. Her name was Sherry. Or Terry. Possibly Janice, but I think that was her middle name… But the name isn't important. What is important is that she was smoking hot. I mean she was FINE! Ass so tight you could bounce a nickel off it, and her face had to be at least a nine. Probably a ten. And I won't even get started on her…other assets. But dude, she was also a marathon runner. Do you know what that meant? Stamina Sammy. She had more endurance than any chick I've met. It came in handy later when we…Well, when we got more acquainted. _

_ But before the fun stuff we were talking about her younger sister who goes to school in California. And do you know where she goes to school? You guessed it! Beautiful Stanford University. And you'd never guess what she showed me… See, her sister had recently texted her some pictures from a party she'd been to. It was a pretty stereotypical college party. I could see a crowd of drunken students behind her sister in the picture, and do you know, I almost choked on my beer when I spotted a familiar face in that crowd. _

_ Tell me Sammy, how's the party scene? Is it as fun as everyone says it is? You sure looked like you were having fun in the picture. Hell, you looked like you were having a freaking blast! You looked so cheerful I actually had to take a moment to wonder if it was some kind of Sam-Double I was looking at… Really though, I think it's fantastic that you're letting you hair down and having some fun. But I am seriously amazed by your ability to attend parties like the one I saw in that picture, but still get straight A's on your midterms. I mean really, how the hell do you do it? Like I said before, I'm impressed Sammy… _

_ But now comes the part where I have to give my obligatory big brother speech. You are doing really well in school. Although I have never understood your passion for scholastics, I have always respected it. I admire your commitment to your education. So now I have to ask…You aren't losing sight of that commitment, are you? I mean, God knows I could never say no to shots and pretty college girls either. But I just want to make sure you aren't going through one of those mid-college burnout phases you hear about. I don't want to hear that you hit the books so hard that you eventually threw your hands in the air, got drunk, and then dropped out of school. You worked hard for that full-ride scholarship Sam., and gave up a lot. I'm just saying that I don't want to see you waste it. _

_ But I do want to hear some stories you know. Now that I got my concerned family speech out of the way, I want you to know that I expect you to write me back giving me all the juicy details from that party. Like, who was the blond chick standing next to you laughing? And what was up with the totally dorky expression on your face? Not to mention the normal stuff, like whose place you were at and how hung over were you the next morning. Oh yeah, I totally expect you to dish like a gossipy teenage girl. _

_ Until then I gotta get going. Dad and I are driving over to a little town in Kentucky to take on a vengeful spirit who seems to get its kicks by forcing people to poison their own dinners. I know. It's just weird, right? Anyway, keep up the good work college boy. I am still proud of my genius brother, even if he looks like a total goon in the last picture I saw of him. _

_Dean_

_P.S. I would look into Blond Girl. She was giving you the flirty eyes from what I could tell. Just saying! _

**Secondary Author's Note: Thanks for reading! I will have part two of this request up very soon. As usual, reviews and requests are totally appreciated! :) **


	59. Impressive

**Author's Note: So here it is! The response letter from Sam to Dean regarding the most recent letter "Familiar Face", fulfilling the last half of the request reannablue gave me. :D I want to thank jojospn, judyann, reannablue, GuestJ, flygirl33, girlinpink44, SPNxBookworm, and mb64 for their recent awesome reviews. And thanks to all of you who read these! **

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ First off, thanks. I worked my ass off this last round of tests. I can't tell you how many hours of not-sleep I had to endure to get those A's, but it was totally worth it. As for that girl you met... Dean, how many times do I have to remind you that I don't need to know so many details about the girls you, uh, spend time with? And I definitely don't need to know how much "stamina" they have. It's just awkward man… Of course I also know that's why you do it. To make me feel awkward. So good job messing with me from a thousand miles away. I loathe admitting it Dean, but your ability to still do that does impress me. _

_ Speaking of impressive, have I mentioned how incredible I think your luck is? Only you would be lucky enough to find a way to spy on me from across the country without having to work at it at all. So some chick really happened to have pictures of me at that party? And yes, I do know which party it must've been, because there was only the one thing I've been to that qualifies as a full blown college party. And just so you know Dean, mail travels slower than text messages. The party happened after my midterms, not before or during. But I still appreciate your concern for my education's future. Really, I'm not even kidding. It means a lot that you do care, even after I left. But anyway, you don't really want to hear this sappy stuff. You were pretty clear that what you wanted was for me to answer your questions about the party. And because I'm such a nice brother… _

_ The party was actually being held at my friend Rebecca's place. We were all celebrating the end of our midterms by doing what college kids do best: Getting drunk and trying not to do anything we regret too much the next morning. And before you get too excited, I'll have you know I didn't do anything humiliating or entirely regrettable that night. Unless you count having my picture taken when I wasn't paying attention. Which apparently you do. I would honestly tell you why my face looked as dorky as you say it did, because I would love to defend myself. Except I never even saw the picture. I'm guessing it was because I was pretty drunk though. And by pretty drunk, I mean I can shamelessly admit that I was hammered. And you did say I looked cheerful... Well, my friend Brendon calls me the Jolly Green Giant when I get too drunk. He says it's because I'm happy, huge, and always sick by the end of the night.  
_

_Speaking of Brendon, HE did something embarrassing and regrettable that night... Now he's a good guy, I swear. But he got too many shots in himself and actually got up on Rebecca's table and started stripping. It took me and two of my other guy friends to finally get him back down. Thank God he never got past his jacket and shirt. And one shoe and sock. He wasn't exactly thinking in a linear fashion... I bet this chick you met had pictures of that too, because I don't think anyone at the party missed that photo opportunity.  
_

_ And you really want to know how hung over I was? That's a little weird, but ok. Remember the time that ghost sent a Dutch oven flying at my head? Yeah, it was basically the same kind of feeling only with a lot more nausea and a lot less time to recover the next day in the car. I seriously had to be to class at eight AM the next morning. Never have I hated a morning more. And that's counting the morning you woke me up by puking on my bed. And before you get all defensive, I know it wasn't your fault and that you had the flu. But that was seriously disgusting, and yet this morning was worse. Have I made my point? _

_ Now to "dish" about "Blonde Girl". Her name is Jessica Moore. She is a sociology major and we have a few classes together. A friend of mine introduced me to her after he caught me staring at her in…now don't you laugh...in the library. I mean it Dean, you better be holding it in! Anyway, she was studying there every day for a whole week while I was there all the time working on a paper. I didn't hide behind a giant pile of books like you imagined, but I did hide behind the one I was reading for the paper. I couldn't help it! You saw her and you have to admit she's gorgeous. So I got nervous. And at this point I know you're laughing, so bite me jerk. _

_ Anyway, we ended up hanging out a lot after my friend dragged me over to say hello. We discovered we have a lot in common. She likes the same kind of music as me, we read a lot of the same books for fun, and she even considered law school herself before deciding the general social sciences were more her thing. She's basically great, and yesterday I finally worked up the nerve to ask her to dinner. You must be right that she was giving me "flirty eyes" in that picture, because she agreed to go out with me. We're going to this place in the city that does all different kinds of seafood, and I'm actually not as nervous as I usually would be. I don't know man, there's something about her that just makes me feel comfortable. Like, we can actually talk for a long time and I don't get awkward or bored. I really like her Dean. I'll let you know how the date goes in my next letter, but right now I've got to go get ready for it. Cross your fingers for me will you? _

_Sam_

_P.S. I know this letter will reach you after your hunt, but I'll still say it… Watch yourself out there ok? Dad too. I don't want to get a call informing me either of you died of self-food-poisoning. I'd be embarrassed for you both. _

**Secondary Author's Note: Thanks for reading! Remember, reviews and requests are awesome. :D **


	60. Your World

**Author's Note: This is letter number 60. (Unbelievable, by the way.) And since it is a multiple of 20, and I am apparently OCD, it is a Castiel letter! :) I received a request recently from girlinpink44, who asked for "a letter from Castiel to Dean right before he agreed to work with Crowley". I know it would be weird for Castiel to be writing a letter in that moment, but I'm ignoring that because I really liked the request. lol So here it is! Castiel's letter to Dean just before Crowley had ever approached him. I also want to thank m1tchells, jojospn, ClassyMuse, girlinpink44, mb64, judyann, reannablue, flygirl33, SPNxBookworm, GuestJ, and Garideth for their recent amazing reviews. And thanks to all who read these! Seriously. I love you all. :D **

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ After I first rebelled against Heaven I was angry. I was angry with you for having caused me to doubt my orders. To doubt the very foundation of my existence. Before you I was willing to fulfill whatever demands Heaven supplied. I never questioned. I was the perfect soldier. But then I met you. I pulled your soul from eternal damnation, and I was fascinated by you. For someone who owed his life to the will of Heaven, you seemed very determined to reject that will. And as I watched you, I saw a good man. A loyal, strong, and brave man. And I began to wonder why such a man would seek to disobey Heaven. _

_ Over time, I began to understand. The more time I spent with you, the more I began to see the truth behind the orders I was given, and to comprehend the consequences of my continued obedience. Because I got to see the way it affected the humans. Your people and yourself. You and the world you loved would suffer if I continued to obey. That is why you would not obey. You would fight, like you always do. You risked everything time and time again for the sake of a world you didn't even feel safe within. A world that, more often than not, rejected you. _

_ But I admired that about you. I admired your selfless dedication, and I wanted to help you. So I fought against my brothers and sisters. I cast myself out of my own home for the sake of yours. And when I did that, only to discover that Lucifer's cage was still opened, I was furious. I almost regretted ever having listened to your guidance. And it seems funny to me now, because now I would give almost anything to hear that guidance once more. _

_ I stand here Dean, in the shade of the trees of your backyard, watching you scrape leaves off of your grass. Watching you lead a life of normalcy and seeing you finally experience the peace you so greatly deserve. Perhaps this time the world has not rejected you. Perhaps this time you have been given a real chance to settle down and enjoy what remains of your lifespan. To have the comfort of family and safety that you have always secretly craved. And who am I to steal that from you Dean? Who am I to intrude on your new-found security? _

_ But I want to. I want to turn to you and ask for words of wisdom. My home is a disaster area, my family is fighting itself, and all the while I am lost. I don't know how to win this battle I have started. Raphael will either kill me or I will lose myself to him. I admit death would be better than bowing to him. Yet if I die, who will stop him? The fate of your world hangs in the balance once more Dean. If Raphael is left to achieve his goals, your world will suffer. This life of comfort you lead will surely be destroyed anyway. So why should I choose to hold back? Why not drag you into all of this conflict again? After all, I know you. I know you would prefer to know what is coming so you could prepare. So you could fight. So you could protect those you love. _

_ But that's just it, isn't it? You have a family now. And woman and a child to love, and to be loved by in return. If I bring this war to your doorstep, I would be placing you all in grave danger. How can I repay you for everything by putting you and your loved ones at risk? Because despite my initial anger at you for having planted the seeds of doubt in my mind, I am also eternally grateful that you introduced me to freewill. Now I know that whatever madness I face, I have the ability to at least control my own responsive actions. And there will be doubt, and regret, and even sadness at times. But there will also be victories. Lives saved because of my choices. A world safe because of my actions. You gave me the confidence to disobey. To make choices and to help people in need, and for that I profess my gratitude. _

_ And perhaps you are one of those lives I can save. Not from Hell, but from being pulled back into the chaotic world of angelic wars waged on Earth. You are a person in need. You need peace and time to recover from the loss which I can see still weighs within you now. Your shoulders are heavy with your memories of Sam. _

_I can give that peace and recovery to you. I can help you. I will not bring my fight to you. I will not ask you to sacrifice any more. Not after you have already given so much. If I am to stop the apocalypse again, this time I will do it alone. I will fight to save this world. Your world. I will do this for you. _

_Cas_

**Secondary Author's Note: Thanks so much for reading! Seriously, have I mentioned how awesome you all are for having supported me this far? I mean 60 letters is about 55 more than I ever dreamed of writing when I started this series, so thanks for all the encouragement, inspiration, and kindness. I genuinely aprpeciate it all! (Oh, and of course reviews and requests are very much still welcomed. :D) **


	61. Truly Sorry

**Author's Note: This letter is based on a request from SPNxBookworm, who asked for a letter from John to Dean regarding the whole "Save Sam or kill him" thing from season 2. It was a tough request, but I didn't want to back down from the challenge. :) So here it is! Also, I want to thank mb64, kingdommast, The Fantasy Junkie 96, girlinpink44, judyann, jojospn, kirkanalo, SPNxBookworm, WomanOfLetters, and Leia 96 for their recent awesome reviews. And thanks again to all of you who read these! :D **

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ I'm writing this letter to you because I know myself, and I know how unlikely it is that I'll find the right time or way to tell this to you in a conversation. And I need you to understand and to know why it is that I'm asking this of you. Why I'm laying such a heavy weight on your shoulders. Because God knows that if I knew of any other options…But I don't. And so I'm forced to do this to you. To ask you to bear the burden of one of the hardest responsibilities I have ever given you. _

_ Dean, there is something not right about your brother. The yellow eyed demon…He did something to Sam when he was just a baby, that night Mary died in the nursery. I don't know exactly what he did. And to be honest, I'm only mostly sure that he did something. There's still a chance he could have been coming for Sam because of something already existing inside of him… But either way, the fact remains that Sam has something…unnatural about him. Something the demon wanted him for. _

_ Those dreams Sam has? The visions he told us about? That's just the tip of the iceberg from what I've gathered. There are others like him out there. Some you've met and some you haven't. They have different abilities and different personalities. But the one thing they seem to have in common is that they all snap eventually and do something awful. Something violent. And they do it using whatever powers they possess. Dean, you already know that Sam possesses the ability to see the future in these visions of his. That ability seems harmless enough, but it's only a matter of time before other abilities start to become apparent. Darker abilities.  
_

_ God knows that I would give anything to not have to say these words…But you are going to have to save your brother, Dean. Save him from whatever it is that makes him a target for this demon. Whether the demon did it to him, or if he was born this way. It doesn't matter. You've still got to save him. Because...Because if you can't do that, you'll need to kill him. _

_ He cannot be left to turn into one of these deranged and murderous psychics I have been hearing about. I love that boy with all my heart, but I could never leave him to become that. You've got to understand that I don't want you to have to kill him. It's a last resort. You only kill him if you find there is absolutely no way to help him. But Dean, you must be able to recognize why he can't be allowed to change into a monster. He wouldn't be our Sammy anymore, and he would be a danger to all the innocent people we try to protect. _

_ I hope you know I hate myself for even thinking about this. For saying any of this at all, especially to you. I spent your whole childhood telling you to take care of Sam. To protect him and keep him healthy and safe at all costs. And now I turn around and ask something so unthinkable of you…I'm sorry Dean. I am so sorry that any of this ever happened. You were such a good kid, and you didn't deserve any of this. More than that, you grew up to be a man I'm proud of. A man who should never have to face what I am asking you to face. _

_ But as much as I would give my heart and soul to be able to prevent you from having to know this. To be able to somehow undo all of this and make Sam one hundred percent ok so neither of us has to worry about what we might have to do… I can't. The world has to come first. The innocent lives we fight for, they have to matter most. And so you have to be prepared to do what is necessary to keep Sam from becoming a threat to civilians. _

_ But if anyone can save him Dean, you can. I know you inside and out, and I know you'll stop at nothing to protect that kid. Often times I admire the way you care for him. I'm ashamed of myself and proud of you when I admit that you've been a father to him. And by that I mean the kind of father he needed. Attentive, patient, selfless. I know you won't rest until you've saved him, because you have never let him down before. And I know that if there is no other option, then you'll love him enough to stop him from becoming something…something he isn't. _

_ I love you both Dean, and I wish there was anything I could do other than hand you this job. I wish I could say I'll be around to do my best to save him myself. But I won't be. After I do what I'm about to do, I have very little faith that I'll be alive in the next day or so. So please Dean, do what you do best, and save your little brother. _

_ And don't forget that I never wanted this for you. For either of you. You're my sons, and I love you both so much. And I am really, truly sorry. _

_Dad_

**Secondary Author's Note: Thanks for reading! I love a good challenging request, so fire away! Also, reviews are incredibly amazing. :) **


	62. Number

**Author's Note: This letter is for ****LoveIsAllYouNeed96**, who requested "a letter from Bobby to Sam after what the demon said in Good God, Y'all." (Season five episode 2, after Bobby got possessed.) She also asked I mention Dean at some point if possible. Well, this is what I came up with! :) I want to thank judyann, jojospn, Leia 96, kingdommast, A Guest, and GuestJ for their recent amazing reviews. And thanks to everyone who reads these! :D 

**Disclaimer: I don't own Supernatural. **

_Sam,_

_ I want to clear the air about some things. Partly because I don't have anything better to do while I'm sitting on my ass here in this damn hospital bed. But mostly because the world is apparently coming to an end, and I can't let that happen without these things being said. So for starters, I need to tell you I know that demon said some real nice things to you when it was riding around in my head. It kept me awake for most of it see, and I heard every word it said to you when it told you to "lose my number". _

_ So let me set one thing straight. I think you are an over-sized idjit and a complete lunatic most of the time…Hell, I still want to smack you for putting me through all the worrying you did... But if you ever even consider losing my number, Armageddon will look like a fancy tea party compared to what I'll do to you boy. You got that? You ain't my blood, but you're sure as hell my family kid, and I'm not giving up on you. Not ever. You made a mistake, and yeah it's a big one. But that doesn't mean that I hate you for it. _

_ And I also want you to know I never saw that whole "killing Lilith starts the end of the world" thing coming either. Who the hell would have thought we'd want to keep a demon alive? Especially that particular demon. Oh, you better believe I wanted her dead just as much as you did. After what she did to your brother? That bitch had it coming in a big way. I never could have guessed we weren't supposed to snuff her sorry ass. _

_ But just because I don't blame you for wanting to kill Lilith does not I'm saying that you didn't do anything wrong. You turned on your brother, trusted a demon, and you got hooked on drugs. That's got 'wrong' written all over it. And if you think that blood was hurting you most, think again. It was hurting Dean and I too, hot shot. We had to listen to you screaming and begging us for help. We had to chain you to a damn cot and lock you up. And it nearly killed you. And if it had, you've got to know that would've killed us too… _

_Now I'm not saying this to make you think I hate you. Like I said, I don't. But I am saying it to make you feel good and sorry for your actions so you won't pull that crap again. I'm saying it because I care about you, and I don't ever want to have to see you so damaged again. After all, it looks like we've got the end of the world to deal with. Last thing we need is to lose one of our best men to something as pointless as drug abuse. Because yes Sam, I still see you as one of our best men. You're a damn good hunter and a damn good person too. And if I get to pick my team mates for this little game of apocalypse-ball, you're on my list boy. _

_ You and Dean both. And by the way, I see how tense you two are with each other these days. He thinks I can't see it, but I can. And believe me, I get it. I know where Dean is coming from…But now really isn't the time for him to develop trust issues with you. You screwed the pooch but you're still someone we can rely on. I know it, and if he don't, then you can tell him from me he's being just plain stupid. We got bigger fish to fry than this family drama, and he had better wrap his head around that. After all, the Devil's on the loose now. We need to stick together, or I don't doubt for a second he'll find a way to use it against us. Let's not give him the chance, shall we? _

_ So you boys watch yourselves out there. The world just got a lot scarier, and that's saying a lot, seeing as it was a damn horror movie to begin with. So just be careful alright? And if you need anything, and I mean anything at all, you call me right up on that number I expect you to keep with you at all times. We clear? Good. _

_Bobby _

**Secondary Author's Note: Thanks for reading! Reviews and requests are completely welcomed and appreciated. :) **


	63. If The Choice Was Mine

**Author's Note:This letter is for mb64 and girlinpink44, who have both requested a letter from either Sam or Dean to either Jared or Jensen. (After "The French Mistake, of course". Now, girlinpink44 pointed out to me that Dean wrote a letter to Dean Smith. So I thought I'd balance it by letting Sam write this letter. Here it is! A letter from Sam to Jared Padalecki sometime after "The French Mistake". I want to thank reannablue, kirkanalo, LoveIsAllYouNeed96, a Guest, ****shirleypositive72, jojospn, mb64, girlinpink44, kingdommast, Guest J, and another Guest for their recent kind reviews. And thanks to everyone who reads these! **  


******Disclaimer: I don't own Supernatural. **

_Dear Mr. Padaleq … _

_Dear Jared,_

_ I'm going to start by quoting my brother here… You married fake Ruby? Seriously? I mean believe me, I get it. She is completely gorgeous. But you actually married her? Then again, I guess you really have no reason not to be ok with that, right? You come from a world where all of this… It's all just pretend to you. It's words on the pages of a script and choreographed fight sequences to be filmed on a sound stage. It's a job, but it isn't THE job, you know? _

_And I have to wonder what it's like for you while you're playing me. I watched some clips of that show when I was researching Dean's…Sorry, Jensen's history in that universe. Everything about the show was dramatic. Even the humor seemed to have an underlying kick to it, like it came from a place of pain. I think it surprised me how real it felt to watch. I mean, obviously all the slow panning sequences of Dean and I crying felt over-the-top… But the fact that almost every moment on the show was steeped in anger, sadness, or helplessness… It was right on the money for how I've felt these past few years. _

_ But to you it must be like a game, being me. To you I'm someone you get up in the morning and choose to be. So if the scene calls for my tears, you cry. And if I'm supposed to get angry, you pretend to feel that anger. If I am ever in unimaginable physical discomfot, you scream like you're hurting. But you're never really hurting, are you? Hell, the worst emotion I bet you actually deal with is boredom in between shots... _

_But my life is nothing like that. Because that man you pretend to be for a living? He's real, and he's me. And I really have to live through all the stuff you only make believe is happening…And part of me wishes I could have just one day where my job was to pretend to be you. _

_Wouldn't that be easy? I wish I could wake up next to my beautiful wife and go to work on some set, and all I had to do at my job was pretend to feel the pain of someone else. Better yet, someone I thought wasn't even real, so it wasn't like I was mocking their experiences with my own interpretation of them. I wish that when I went to work, there were fluffy crash pads every time I needed to get tossed around. And wouldn't it be awesome to be facing off with a guy in a costume instead of the real deal? And I'm not even going to start on the money. God knows my real job doesn't pay nearly enough. In fact it pays me in bills, what with all the hospital trips I've suffered through for my line of work… _

_ But the one thing I don't wish I had that you do is that crappy relationship with Dean. Sorry, Jensen or whatever… You have a wife and a mansion, and even some kind of alpaca farm out back… You have a safe job that's well-respected and even fun. You have practically everything! But you don't have enough to make me chose your life, if the choice was mine. _

_ You play me on a daily basis so I'm betting you know. And maybe you're actually jealous of me for it. I mean, if you knew I was real, I think you'd wish you had the one good thing I still have. Because for all the fancy friends I'm sure you've got, and for all the people who I'm sure love you, I didn't see a single one of them as close to you as Dean is to me. And as much as all those tears and beatings are real for me and not for you, I wouldn't trade them for what you have. Because you might have a lot, but you don't have it all. You don't have my brother. _

_Sam  
_

**Secondary Author's Note: Thanks for reading! Reviews and requests are great, so don't be shy! :)**


	64. Choice

**Author's Note: This letter is for a Guest, who requested "a letter from John telling the boys that he has another son (Adam)." Well, I thought this was a pretty good idea, so here it is! In my head, this letter was written by John while he was in the hospital sometime during 2X01 "In My Time Of Dying". I want to thank jojospn, judyann, girlinpink44, kingdommast, kirkanalo, ClassyMuse, mb64, reannablue, flygirl33, WomanOfLetters, and GuestJ for their recent wonderful reviews. And thanks again to everybody who reads these! :D**

**Disclaimer: I don't own Supernatural. **

_Boys,_

_ I have some interesting news for you. To be honest, I don't think I was planning on ever telling you this, but seeing as this might be the end for me…Well I figured I owe you both the truth, and I owe it to Adam to not deprive him of his brothers. Well I guess I kind of let the cat out of the bag right there, didn't I? Sam, Dean, you are my sons and you both mean the world to me. But you aren't my only children. You have a half-brother. His name is Adam Milligan, and he lives in Windom Minnesota. _

_ I know this is probably coming as a huge shock to you both. And I can imagine you're pretty pissed at me for having not shared this information with you sooner. I promise I'll explain everything, but first, let me tell you a little bit about him. It might even answer some of your questions just to hear this…_

_ First, he's about sixteen years old right now, and he is an AP student in his high school. He likes baseball, and fishing, and he's hoping to grow up and become a doctor. He's got a bunch of friends, and a mother he loves dearly. They live in a nice little suburban community, and he even has a pet lizard named Fred. Basically, he's as normal as a kid can be. His life is normal, his friends are normal, his ambitions are even normal… He never has to salt his doors and windows, or clean guns every night before bed. He doesn't speak a word of Latin either. He took French 1 as his foreign language in school because he "thought girls would like that". He's a good kid. A good, smart, normal kid._

_ And I wanted to keep him that way. I know I did wrong by you boys the moment I dragged you into this life. I got so obsessed with keeping you trained and ready to protect yourselves, I lost sight of the fact that you were just kids. And by the time I fully realized the weight of what I put on both of your shoulders, it was too late. You're hunters now, and I can't undo that. But with Adam I was left with the same choice, and I wanted to make the right one this time. _

_ I met his mother after a hunt in Windom. She was an ER nurse, and I was a patient of hers. We…hit it off, so to speak. I left town after that, and it wasn't until a good fourteen years after the whole event that she called to tell me I had another son. And so I was faced with a choice. I could chose to go to him and his mother, expose them to the reality of the world, and train the boy to be strong and capable like you boys are. Or I could choose to let him live his peaceful life. To pretend I wasn't a hunter when I was around him, and to give him the normalcy I deprived you two of. I chose the latter. _

_ It wasn't fair that he got to have the things that you both needed, but were never given. Sam, you especially should be fuming right now. But please take a moment to consider my perspective. I'd screwed up with you both. Not that I'm not incredibly proud of who you guys are, because I am, but I wasn't exactly father of the year when you were growing up. I knew I couldn't be that for Adam either, but at least I could stop myself from ruining his childhood by placing him in constant danger. I was just trying to learn from my mistakes. I regret having dragged you boys into this mess, not because I think you turned out bad. Like I said, I am so proud of the both of you. But because I am your father, and it's my job to keep you safe. And I failed at that job. _

_ I told myself I was trying to protect you by making you both capable of defending yourselves. Making you aware of the threats so they couldn't catch you off guard. But what I should have done was protect you from those threats myself, and leave you both out of it. You've been injured more times than I can count, and nearly died a few times too… That's on me, and it never should have happened. _

_ So I decided to do it differently this time. I never told Adam about hunting, or monsters, or anything else out there. I took him to a baseball game on his birthday, and maybe fishing once or twice. I encouraged him to go to medical school after high school. I let him be as normal as could be. _

_ So I'm genuinely sorry I can't take back what I did to you both as children. That I can't reverse the clock and let you grow up as average kids yourselves... But I wouldn't make that mistake again. So yes, you have a half-brother. A younger brother who is as run of the mill as they come. And I'm asking you both to keep it that way. Feel free to visit him. Like I mentioned, I think I should stop keeping you guys apart, now that I won't be in the picture much longer. But just…Don't spoil him, ok? _

_ I trust you won't. Sam, you would never force that on someone. That much I know. And Dean…I know you would have given an arm and a leg to have kept Sam safe from even knowing about this stuff. You're an amazing big brother to Sammy, and I don't doubt you'll be that way with Adam too. So thank you, and I really am sorry for this. I'm sorry for everything. _

_ Dad_

**Secondary Author's Note: Thanks for reading! I have been loving the requests I'm getting, so keep 'em coming! Also, reviews are very much appreciated. :)  
**


	65. Still Are

**Author's Note: This letter is based on my own ideas. I was looking at the letters I've already done, and I realized that I've done several from Dean to Cas, but never one from Sam. So this is a letter from Sam to Castiel, written sometime shortly after 7x17 "The Born Again Identity", after Cas takes on Sam's crazy. It is my belief that Sam, being the sensitive guy that he is, would have felt bad for Castiel having to take on his craziness. Even though Cas kinda earned it. :P I want to thank the guest "TG", jojospn, kingdommast, judyann, WomanOfLetters, mb64, and SPNxBookworm for their recent awesome reviews. And thanks to all who read these! :)**

**Disclaimer: I don't own Supernatural. **

_Castiel,_

_ I'm sorry, you know that? You're stuck bearing the burden of all my time in Hell, and it doesn't seem fair. Yeah, you messed up and broke my wall, but after all the times Dean and I have done stuff to you? After everything we've put you through? It seems unfair that you would have to go through this as penance or something when we never did. You always forgave us right away. You always returned to us and continued to help us. I mean I wouldn't even be out of Hell if it wasn't for you. And I'm not complaining that you couldn't get my soul out too. You walked into Lucifer's cage to save me, and I'm grateful you had the nerve just to try. _

_ I guess I'm grateful for a lot. Like how you never did anything to hurt me when we first met. You weren't exactly in our corner yet, and I know Uriel at least wanted my head on a stick. But even though the host of Heaven clearly hated me and saw me as "an abomination", you still treated me with the same respect you showed Dean. And instead of trying to stop me yourself from doing the dark stuff I was doing, you gave Dean the opportunity. Yeah, it all went belly up in the end, and maybe you should have stopped me yourself. Maybe it would have made a difference… But I'm still grateful that you didn't. That, in your own way, you tried to save me instead. _

_ And do you remember when Anna wanted to stop the apocalypse by killing me? I kind of wanted her to succeed, because I figured she had a point. If she could really take me out of the equation for good then Lucifer could never win. The world would be safe and at least I'd have died cleaning up my mess. But you wouldn't hear it. Not because you didn't believe it could work, but because you wouldn't sacrifice my life if you thought there was any other way to solve the problem. It was stupid to defend me like that, because it risked the whole planet for the life of the man who set Lucifer free to begin with…_

_ But as irrational as your loyalty to me in that situation was, it still meant a lot to me. I think that was the first time I was sure you were a part of my messed up little family. Because only Dean and Bobby have ever showed that much stupid dedication to me. And after that, you only continued to prove you were family. You came every time we called. You fought on our side in more seemingly futile fights than I could count. You sacrificed and bled and eventually even died for us. _

_ You know, I remember the day you stood with Dean and Bobby at Stull Cemetery. I was watching everything, screaming away in my own head while Lucifer had control. I watched when you threw that Holy-oil Molotov at Michael, which was great by the way. And suddenly Lucifer was pissed. Talk about a messed up family... You know I could feel Lucifer actually care that his brother had been hurt? He wanted to kill him, but he didn't want anyone to hurt him… It was really weird. _

_ But before I could laugh at the hypocrisy, Lucifer turned on you. I tried so hard to stop him, but I couldn't. And then you were just gone. Exploded everywhere, and it was awful. You had given everything to stand by us, and you were rewarded with such a brutal end. But the worst part was that you did so willingly. It wasn't even like Ellen and Jo, because at least they hadn't known going in that they would die that day. But you knew as soon as your threw that bottle. It was your choice, and you chose to die for us. _

_ And after you had literally died saving us and the world…You came back. I don't just mean that you came back to life, but back to us. You could have chosen to never speak to us again and it would have been understandable. I mean no one could fault you for wanting to avoid the guys who got you killed. But instead you joined right up with us again. You fought by our sides, again. And even while your home was tearing itself apart, and you barely had time to think, you somehow always found time to come when we really needed your help.  
_

_ So whatever bad choices you made...Whatever your mistakes... It doesn't change that you had our back through everything up until then. And this seems like a pretty poor way to repay you. So I'll say it again… I'm sorry. And I want you to know that if we can't find a way to fix what's happening to you right now, I will always see you as the friend that you've been to us. The family to us that you still are. _

_Sam _

**Secondary Author's Note: Thanks for reading! This was just for fun, but I am definitely still fulfilling requests. So definitely keep sending them my way! And reading the reviews you guys leave makes my day, so don't be shy. :) **


	66. Heartless

**Author's Note: This letter is for ****Er-BearG32**, who suggested "one from season 6, from Dean to Sam (the real Sam, not Soulless Sam), while his brothers' body is wandering around soulless and his soul is locked in the cage". I actually just re-watched the whole part of season 6 in which Sam is souless, so I loved this request. :D I want to thank kirkanalo, kingdommast, shirleypositive72, judyann, mb64, girlinpink44, Chlorine, GuestJ, writerofthelord, reannablue, and Er-BearG32 for their recent reviews and support. And thanks to everyone who reads these! :)  


**Disclaimer: I don't own Supernatural. **

_Sammy,_

_ He killed a spider today. He just reached over with a tissue and smooshed the thing onto the table like it was nothing. And I almost wanted to cry Sammy, because you would never have done that. I'm not one to freak out over a dead spider, but it was like the last straw or something. Or the last crack in my pretty feeble emotional dam. _

_ I thought I was handling this, you know? The whole, "the guy who looks exactly like the little brother you thought you'd lost forever and were so relieved to have back, except he doesn't have a soul, so he isn't really your brother after all" thing. But having to look at him and see you, but not you…There is darkness in his eyes that you never had. Not even when you were hoped up on Demon crack. He has this callus expression of perpetual indifference… It's too much._

_ Half the time I want to beat the crap out of him for being so damn insensitive. The rest of the time I want to shake him until he somehow just grows your soul back. Until you're fully back, and I don't have to see your face so devoid of that stupid compassion I've always teased you about. I'm telling you, I'd give anything to see your sappy puppy dog eyes right now. I'd even pay good money to have you try and get me to talk about my feelings. Because as awkward as that always was for me, it still meant you cared. I guess I never realized how much it mattered to me, you caring, until it was gone. _

_ But I'm sticking with him even though it hurts like Hell. Because Hell is the problem, isn't it? You're still in Hell Sammy. You're still there, and it's killing me to see robo-you walking around all healthy and carefree, when I know the real you is still stuck in that pit with the Devil and his pissed off cocky brother. So I'm not leaving him, because I'm not giving up on getting you back. You told me not to go poking the cage because it was too risky? Well I'm going to pretend there was an unspoken exception to that. Something like, "Except if I pop up as just a body and all my memories, but not an ounce of the humanity in me that I used to have". _

_ I dare you to tell me I'm wrong for not being able to go through this any longer. There's no way you could ask me to continue to see you like this and not do everything in my power to fix it. I'm getting you back. The real you. The you who catches spiders in paper cups and puts them back outside of the motel because "they're living creatures too". The you who begs me to share-and-care when the going gets tough because you know I won't do it on my own even though I need to. The you who I have spent practically every moment of my life with, and I can trust with everything and anything. _

_ I genuinely can't trust him Sammy. He basically threw me to a damn vamp the other day! I mean the guy actually stood there smirking as I got turned into a bloodsucking monster. (There was a cure, don't freak out.) See? I miss that. I miss when you would freak out. When you'd panic and get all dewy eyed, and then hug me or something gushy like that when I was clear of whatever the danger was… Not him. He used me as a means to an end and didn't even flinch. _

_ God I miss you Sammy. I miss you with everything in me. But I'm fixing this. I'm using him as a means to an ends now. It's the only thing keeping me from getting as far away from him as I possibly can… I need him because, as much as he isn't you in the slightest, he's still who you need to come back to. And I am bringing you back even if it kills me. Because whatever the cost, it can't be worse than seeing you so…heartless. It can't be worse than this. _

_Dean_

**Secondary Author's Note: Thanks for reading! I got so many amazing requests after the last letter, it was completely awesome! Thanks so much, and keep them coming! And your reviews make my day, so feel free to share your thoughts. :) **


	67. Failed

**Author's Note: This letter is for Chlorine, who requested "a letter to Azazel in which Sam essentially tells Ol' Yellow Eyes, 'You're dead, I'm going to save Dean, you lost, so suck it.'" Well I liked that idea a lot, so here it is! One aggressive/victorious letter from Sam to Azazel, written shortly after the season 2 finale. :) I want to thank judyann, kirkanalo, Er-BearG32, reannablue, kingdommast, WomanOfLetters, mb64, jojospn, girlinpink44, and SPNxBookworm for their recent amazing reviews. And thanks to everyone who reads these! **

**Disclaimer: I don't own Supernatural. **

_Yellow Eyes,_

_ So I think I owe you a giant "I told you so". It's from me, my father, and my brother. I mean we told you over and over that we weren't going to let you win... And I know for a fact my brother had sworn he would kill you. Well I guess he made good on that promise, didn't he? How does it feel having been defeated by the guy you said was no threat? The guy you actually resurrected because you thought he wouldn't cause you any trouble… Well I bet it doesn't feel like much seeing as you're a doornail right about now. _

_ Man, it feels good to finally say that! You're dead you stupid, arrogant, spineless, evil son of a bitch! You're dead, and my brother and I are still alive. And you know what? Even though he isn't alive with us, our dad still turned up for the big showdown. He still got the chance to help us take you out. So in the end I think the score is Winchesters: everything, You: nothing._

_ You're nothing anymore. Not even remains, because that body you were in belonged to someone else. And that's just how I want you. I want there to be no proof you ever existed. No proof you were ever even a thing, because you don't deserve to be remembered. You are a worthless scum bag and if nobody ever utters your name for the rest of eternity it would be too soon. You deserve to be forgotten, forever. _

_ You fought so hard to rule the world. To be known as the king of damnation, with your little army of psychic children whose lives you destroyed… And you know what? I might do my best to never think about you again, but I will definitely choose to remember those people. Because I don't blame them. Andy, Max, Ava, even Jake… They were all manipulated and tortured by you into doing bad things, but it wasn't who they were. They were mentally abused probably since they were babies. And they didn't have the training I did, so of course they weren't going to cope well. They were all doomed to burn out, go crazy, or just plain die. You ruined them, but I won't ruin their memories because of what you did. You don't even get that small victory. _

_ And by the way, you kept saying you were "betting on my horse"? You were rooting for me to win. That's why you got me training again, right? That's why you shoved me back into this lifestyle by murdering the woman I loved… Well it looks like the joke's on you. Doesn't it seem odd to you that I'm the only one of your psychics that didn't turn dark at any point? I'm the only one who didn't choose to use their "gifts" at all. I think it's because of the way I was raised, and the way I've continued to live. The life I've lead, well, you thought it would harden my heart. But in the end it only solidified my resolve to fight the darkness you planted in me. And guess who helped the most with that? _

_ See, as grateful as I am for this little streak of stupidity, I've got to point out yet again that you were dumb for bringing back Dean after that crash. But that wasn't the first time you had underestimated how much he could mess up your plans. You should've left us to stay apart. Because if there's anyone who gives me the courage and strength to stay good, it's him. It's always him. He has done everything in his power to keep me on the straight and narrow since the start. He's been someone good I could look up to my entire life. So when you nudged us back into hunting as a team, you basically handed me the best weapon I could ask for. You gave me the biggest source of moral strength and encouragement you possibly could have. _

_ And I bet you'd be pointing out that Dean sold his soul for me if you were alive right now, just to try and sour my moment. But don't you dare think that's your consolation prize… It's not. Yeah I feel like crap knowing he did that for me, but do you know what I don't feel like? I don't feel like sitting around waiting for my brother to get dragged to Hell. Instead I feel like finding a way to save him. And the last time I felt like doing something, like helping my family kill your sorry ass for example, I did it didn't I? _

_ So you better believe I will tear the world apart until I have found a way to undo Dean's deal, and I will not stop until his soul is safe. So suck it Yellow Eyes, because you lost this one. In fact you lost all of them. You just plain failed. _

_Sincerely, _

_Sam Winchester  
_

**Secondary Author's Note: Thanks for reading! Reviews and requests are always completely great. :D **


	68. People

**Author's Note: This letter is for writerofthelord, who gave me this request: "Back in season one, during the episode Faith, Sam and Dean met a girl named Layla who was dying of cancer. She was going to be cured with the whole reaper trick, but because the reaper would kill Dean in return, they had to stop it, and she wasn't healed. Dean promised her he would pray for her. I was wondering if maybe you could write a letter from Dean to Layla, after this whole situation?" I personally LOVE the episode Faith, so I was more than happy to oblige. :D This letter was written by Dean sometime mid season 2. I want to thank kingdommast, girlinpink44, judyann, twomoms, jojospn, mb64, reannablue, SPNxBookworm, and GuestJ for their recent amazing reviews. And like always, thanks to everyone who reads these! :) **

**Disclaimer: I don't own Supernatural. **

_Layla,_

_ I prayed for you again today. I pray for you most days even though I don't know if you're still… around. And I know that sounds like my prayers aren't fueled by religious faith, but I guess that's because they're not. I'm not a very "faithful" guy. I think I pray for you based more on hope and dedication than anything else. Hope that you're ok, and dedication to trying to undo what I did to you. _

_ I know you don't understand why I couldn't let the reverend heal you that night. And knowing that is made even worse because I know you aren't even mad at me for what happened, though you'd have every right to be. It makes me wish even more that I could fully explain, but even if I did you probably wouldn't believe me. I guess I'll just sum it up by saying the reverend wasn't the man you thought he was. Yes, he was technically healing people, but he definitely wasn't saving lives. And I hope you know that I wish he had picked you that day and not me. I didn't ask to be healed, and I didn't even want to be. It's just plain unfair that I got the lucky draw and you got the losing hand. Especially because you deserved to be healed a lot more than I ever could. But I'm not really writing you to go over old regrets, and I have a feeling that you wouldn't want me to anyway. _

_ Do you remember when you told me that you were supposed to have faith even when miracles didn't happen? Well I think you're right. Understand that in my line of work, I see nothing but tragedy, loss, and pain. I see people die all the time, and when it happens they're not exactly lying peacefully in their beds… And I guess it's for that reason that I've never had the ability to muster up the kind of faith you have in God and miracles. I see innocent people die at the hands of real evil, and I just can't find it in me to believe some entity of pure goodness allowed it to happen for some "bigger picture" reason. But what you told me made me realize I could still have some kind of faith. _

_ I have faith in people. I believe in people doing their best to do the right thing, and I have faith in my family and friends. Because when the miracles don't happen…Well it's always been people that have helped me pull through it. When my dad died a little while back, I thought I was going to crumble inside and never recover. But I didn't, because my brother and our Uncle Bobby wouldn't let me. They kept me going. Sometimes forcefully and sometimes by just being there when I needed it. But they saved me from total collapse. _

_ And every time I've been scared or hurt or suffering, it's a person who shows up to help me out. My family helps me bear the burden of my job, and my friends patch me up when I'm broken. Heck, I've even relied on the assistance of complete strangers in the past. So when the Holy Host doesn't feel like snapping his fingers and making it all ok, that's alright. Because I know I have people I can count on to help me anyway. They might not be able to make all the bad stuff in the world vanish, but they'll give it all they've got to at least make it a little better. Basically, I suppose you're right. If you're going to have faith, you've can't just have it when miracles happen. And in my life the non-miracle stuff is pretty much always. So it's about time I found something to put my faith in to help me through the darker times. And you made me realize that. _

_ So this letter is meant to thank you. I know that what I'm saying isn't really what you were implying when you spoke to me about faith, but I still think you'd be happy to know you helped me in some way. So wherever you are, and I'm still hoping you're out there alive and kicking…Thanks. For helping me to see what I can always believe in. And even though my kind of faith doesn't have to do with God's will, that doesn't mean I'll stop praying for you. I haven't yet, and I won't now. Because I want you to know that you can have faith in people too. I can't promise that my prayers will help you, but at least you'll know there's someone out there who cares enough to try. _

_Dean Winchester_

**Secondary Author's Note: Thanks for reading! It just hit me today that I've done nearly 70 letters, and have more than 500 reviews. It's absolutely incredible, and I couldn't have done it without all of you. Thank you so much, and feel free to keep the reviews and requests coming! They have made all of this possible so far. :) **


	69. Curious

**Author's Note: This letter is for kingdommast, who recently left me this wonderfully unique and challenging request: "I would like a letter from Death to Dean explaining why he likes him." I couldn't say no to something as creative as that! So here it is. A letter to Dean, from Death, written sometime shortly after 7X01 "Meet the New Boss". I want to thank kirkanalo, jojospn, kingdommast, writerofthelord, mb64, girlinpink44, SPNxBookworm, and WomanOfLetters for their recent great reviews. And thanks to everyone who reads these! :D **

**Disclaimer: I don't own Supernatural. **

_Dean Winchester,_

_ I see you successfully coerced your angelic counterpart into returning all those nasty souls he had consumed… Good work. Although, I will point out that you could have avoided all of this nonsense had you heeded my original warning about the situation. And do not give me that stream of excuses I know you have waiting on the tip of your tongue. My clues were as detailed as they could be, and you simply did not pay them the amount of attention you could have. _

_ The raw nerve you possess… What makes you assume you can indicate that I had owed you more detailed information? You were speaking to Death itself, and you really choose to imply that it owed you something? Honestly Dean, you are setting yourself up for the obvious with that kind of thinking…Is it not clear that the only thing I owe to you is your own demise? You should be grateful you have lasted so long, given the numerous times your life has nearly been extinguished. And do not get me started on how incredibly frustrating that has been for me. My poor reapers, all working overtime to clean up the mess you and your brother create every time you fail to perish when your time is up. _

_ But as enraging as I find your apparent inability to stay dead, it is this quality in you that caught my attention. For a creature so seemingly simple minded and messy, you do a remarkable job of finding creative ways to outwit the plans the universe has laid down for you. And so when that petulant child Lucifer bound me to his will, I found myself believing that I could place my trust in you to find a way to free me. You. A blundering bundle of emotional damage and alcoholism, and yet you did not fail me. You did what it took to save the world, myself included. And in the process you created yet another massive ripple in the fabric of fate, but at least that time I had anticipated the consequences. _

_ And then you came to me over a year later and requested from me a favor. You actually tried to use my ring as leverage which I found to be almost adorable, I must admit. And I struck a deal with you that you should wear my ring for a full twenty four hours in exchange for my retrieval of Sam's soul. Although I loathe admitting it, you were right. I did know you would fail to wear the ring for the entire day. Furthermore, I knew you would be unable to kill the little girl right out of the gate. But I intended for you to go through that experience so that you could see a tiny sliver of the trouble you cause me every time you go rearranging destiny. _

_ But I always intended to collect Sam's soul, no matter what the outcome of your challenge was. I believe you had suspected from the start that I had assumed you would fail. True to your nature, you chose to point this out in a belittling and insulting manner. And though I was irritated by your snarky attitude, I still had to marvel at your bravado. You never cease to hold your head high. I have reason to believe you would do so in front of God Himself, so it shouldn't surprise me that you would have no trouble mouthing off to me. And still, I went to retrieve your brother's soul for you. _

_ And then there was our most recent encounter. You are either suicidal or delusional, thinking that binding me was a wise plan. And yet you live. I admit I am still somewhat stumped as to why. Why have I helped you on so many occasions? Why have I not smote you for your insouciant disregard for my power? I think, after writing this, the answer has become clearer to me._

_ It is because I appreciate your defiant nature. Being Death, I am so used to every soul bowing before me in fear of my might. But you do just the opposite. You essentially mock my power just by existing. And perhaps I need that to keep things interesting. Mine is a long and repetitive life. You are the thing that provides me with that little spark of change I secretly crave. You mix up the pattern. And although it makes things difficult and frustrating, it also makes them somewhat entertaining. _

_ I am impressed that you have managed to place the world in mortal danger so many times, and yet you continuously pull through in the end and fix everything. Or at least you have fixed the majority of the problems so far. Those Leviathan will be no fun at all for you to deal with. However, I find myself feeling confident that you will manage. And I will certainly be curious to see how you do it. Because that is what it all comes down to, isn't it? You are a curious thing, Dean Winchester. And to a thing as old as me, having my curiosity sparked is a rare event. I am sure we will meet again. Until then, please don't make me regret indulging my fascination by letting you live. _

_Death_

_P.S. I recently consumed a deep-fried Twinkie. I recommended you do the same sometime in the near future, before the chance is gone. _

**Secondary Author's Note: Thanks for reading! I still love requests, and reviews are immensely appreciated. :D **


	70. Thanks Dad

**Author's Note: This letter is for mb64, who gave me an awesome request not long ago. She said she wanted "a** **letter from Dean to John sometime after Dean gets the Impala. I'm thinking happy memories that he has about the Impala (the army men/legos, sleeping in it, learning to drive etc.). And happy, non-angsty memories if possible please!". Well, I did my best! I want to thank mb64, shirleypositive72, judyann, kingdommast, jojospn, girlinpink44, twomoms, SPNxBookworm, and GuestJ for their recent amazing reviews. And thanks to everyone who reads these!**

**Disclaimer: I don't own Supernatural. **

_Dad,_

_ I wanted to show you how much it meant to me, you giving her to me. It's seriously the best gift I've ever received and I swear I'm not even exaggerating a little. I've loved that car my whole life. I grew up in her, learned to drive in her, and now I get to call her my own. It's amazing and I really appreciate it. I mean, do you even realize how many great memorizes I have tied in with that baby? _

_ Like, I remember the first month after you took Sammy and I on the road with you. You weren't used to credit card scams yet, and we didn't always have the money for a motel. But that didn't mean we didn't have a place to sleep. I guess the driver's seat wasn't the comfiest place for you, but when I was littler that back seat was perfect for sleeping… I used to just stretch out on her cool leather, and curl up under my jacket next to Sam's car seat. I would stare up at the roof and listen to the sounds of whatever was outside where you'd parked her, and I'd be asleep before I even knew it. And I'd wake up the next morning to you grumbling like nobody's business about "stiff necks" and "no leg room". But I'd feel well rested and ready to face the day. I still do you know, when I wake up in her… Every time I sleep in her, even if I need to crash in the front seat instead of the back…I always sleep soundly and wake up feeling great. _

_ And then there's the fact that she was my playground all through my growing up. Most kids take their toys to their rooms and play, but more often than not my room was in her backseat while you drove across the country looking for cases. Don't get me wrong, I'm not complaining. It was pretty fun owning that backseat. When Sam was a little older, we'd play "war" together back there. We had those little plastic army men you picked up for us from that dollar store in Milwaukee, and we'd line them up between us on the seat. We'd try and balance them of the door handles too, but when the car was moving that was pretty useless… Until Sam came up with a solution for that. He stuffed one of his shooters in the ash tray his door's handle. It wouldn't fall anymore, but it wouldn't come out either. In fact the little guy is still stuck back there. Ready to shoot anyone who needs to put out their cigarette I guess...  
_

_ Of course I would bring my toys up front sometimes too. I dropped a bunch of my Legos in the vents once. They fell right through to the radiator. Damn things still rattle every time we turn up the heater… But I guess I like that sound. It reminds me of my younger days when the greatest accomplishment I could imagine was stuffing little colorful blocks into random openings in my dad's car. But I got older, and eventually the day came when I was old enough to drive her. Not legally of course, because I'm pretty sure there isn't a single state that allows a thirteen year old to drive. But where's the fun in following the rules anyway?You thought that was as good an age as any, and I sure as hell wasn't going to complain. I'd dreamed of that moment practically my whole life! _

_You took me out to an abandoned lot in the middle of nowhere-ville, gave me a smirk, and told me to trade seats with you. I almost thought you were joking until I saw the look in your eyes. You were as excited as I was, and you had this hint of mischief about you like you'd been planning this. I'm pretty sure I grinned like a total doofus at that point, but I couldn't help it. Then we spent the whole day going over how to control the wheel, and how to gain and reduce speed without causing the car to jerk around. No abrupt stops or take-offs, just smooth sailing. The whole time you were giving me instructions, I felt like the king of the world. Behind the wheel of that Impala… I just felt right, you know? And after the day was done and I was finally managing her with no troubles, you had me throw her in park and trade our seats back. _

_ But the best part of that day was while we were driving home. You glanced in my direction and said one of the best things you ever said to me. You said four simple words: "You did good kid." It wasn't the words so much as it was how you looked when you said them. You just looked so damn proud of me I could barely get out the word "thanks" in response. I think you were proud because for once we got to do something normal. I know we're hunters, and believe me when I say I understand how important the job is. But I also know you like to have the occasional chance to just do something regular. And on that night, it was teaching your son how to drive. To this day that's one of my favorite memories. _

_ That and the first time you ever let me get up under her hood with you. It was an easy enough task, just tuning the carburetor. But I was eight years old, so it felt like I was being instructed on how to diffuse a bomb. I was so freaking careful the whole time, never doing a thing you didn't tell me to. You were a God in my eyes for that hour and a half, and I wasn't about to do anything to mess up the moment where you let me join you in the sacred act of mechanical tuning. And when it was done I felt this intense surge of awe and accomplishment. In all honesty, I think I knew right then and there that cars were a passion for me. But no car is better to work on than Baby. There is something so perfect about taking a day to keep her in order…_

_ Anyway, I guess what I'm trying to show you by writing all of this is that I really do love that car. And the fact that you entrusted her to me…It means everything to me and I am more grateful than you could imagine. I promise you I won't mess her up. I'll treat her right, because she's the best damn car in the world and you and I both know it. So for lack of a better way to put it, thanks dad. This is genuinely awesome. _

_Dean _

**Secondary Author's Note: Thanks for reading! Phew... This was letter number 70! I am still in total shock, and I owe this awesomeness entirely to all of you, so thank you so so so much! Keep the reviews and request coming guys, I seriously love them! :D Also, I want to give everyone a heads up: I am going on vacation from Monday the 5th through Thursday the 8th. Sadly, it means I won't get to post any letters during that time. :( But I will be back at it on Friday, so woohoo! Anyway, thanks again!  
**


	71. Whatever It Takes

**Author's Note: Woohoo! I'm back from vacation, and I'm feeling refreshed and ready to write some more letters! Thanks so much to all of you who left me well wishes for my trip. I really appreciated it! :) So this letter was requested by GuestJ who said, "How about a letter written by Dean to Sam after Sam was first locked in the panic room explaining his statement to Bobby "at least he'll die human"". I thought that was a great idea, so here it is! This letter obviously takes place near the end of season 4, sometime during "When the Levee Breaks". I want to thank SPNxBookworm, twomoms, girlinpink44, judyann, flygirl33, jojospn, mb64, kingdommast, GuestJ, and Lewlou15 for their recent awesome reviews. And thanks again to everybody who reads these! :D **

**Disclaimer: I don't own Supernatural. **

_Sam,_

_ I can't believe this whole time I thought Ruby was manipulating you to set you up for something dark. Boy, I was slow on the uptake wasn't I? She'd already gotten you to the dark place a long time ago, and I doubt she even had to manipulate you much to do it. I mean you are seriously off the reservation…Demon blood Sam, really? After what that stuff cost our whole family? After Yellow Eyes killed mom to feed it to you, and even after dad and I fought so hard to protect you from its side-effects? And that was just a few drops when you were a baby! That whole mess over a few tiny drops, and then you go and decide to start chugging the stuff on a practically daily schedule. And yeah, you chose to this time. No one forced it on you. The circumstances didn't require it. You just chose to dive right in. _

_ Man, what happened to my little brother? Apparently I was gone for just a few months, and he started meeting up with demon pushers and volunteering to become a tweaker… And for what? To kill Lilith in revenge? I get it that she killed me dude, but I'm back now. I've been back for a long time. And that bitch, scary and dangerous as she is…Well I'd still rather let her live than watch you die in pursuit of her. And I don't think she'll actually kill you. Because I think at this rate she won't even have to. You're killing yourself for her, and you don't even see it. _

_ See, I was talking to Bobby about what this whole demon-detox thing could do to you. Both of us are scared you won't survive it… But then again, if you keep at the demon blood it'll kill you anyway. Not literally, but everything that makes you who you are will be gone. You'll be just another Ava, or Max, or Jake. They were as bad as monsters in the end Sam, and I'll be damned again if I let you go down that road too. Sure, as humans we're flawed and we all make mistakes. But that is still a lot better than the alternative. So I told Bobby that I would rather you die human than live on as some kind of twisted shade of who you once were, and I meant it. I would give just about anything for you. I went to Hell for forty years so you could keep living, so you know I'm not all talk. But I won't let you become one of the things we hunt. I won't let you turn into the freak you've always been so convinced that you are. _

_ And I hope you know you're wrong… Every time you tell me you're sure I think you're a freak too? Because I don't. I might think you're a giant bucket of barely managed PTSD and aggression, and I might even actually call you "freak" now and again. But I definitely don't mean it the way you think I do. You know what you are to me? You're the little boy who needed help pouring milk into his Lucky Charms, and who used to want me to plug a nightlight into the wall of every motel we stayed at. You're the slightly gawky teen who stayed up into the wee hours of the morning after a hunt to study for his SATs, and who got nervous asking girls out so he'd ask for my advice. Yeah, when I see you now I see all of that too. To me, you're the whole picture of the person I've looked out for since I carried you out of our burning house. You're Sammy, plain and simple. _

_ And I know you think I've got some overprotective big brother complex going on. I won't deny that's probably true… But I don't think you see the other half of that. You are the 'kid' I've always had to protect, but you're also the person that's kept me sane in this nightmare of a world we live in. As long as I've had you to look out for, I've had something to keep me focused and grounded. As long as you've been on my team, I've known I could tackle all the crap life has thrown at us. I need you as much as you've ever needed me, and probably even more. _

_ So I hope you understand that I can't lose you to this. I've got to do whatever it takes to keep you the person I've known my whole life. To help you stay that shoulder I've leaned on every time you've leaned on mine. Like I told Bobby... If this cold-turkey thing kills you, and believe me when I say that would kill me too, at least we'll both die exactly who we've always been. Humans to a fault, but brothers to the end. _

_Dean _

**Secondary Author's Note: Thanks for reading! I've got a seriously awesome list of requests in line here, and some pretty fun ideas from my own head too. Feel free to keep adding to my list! I'm totally loving it. And your reviews make my day, so feel welcome to share your thoughts! :) **


	72. What Happened To Your Little Brother

**Author's Note: This letter is for the awesome jojospn, who requested a response from Sam to Dean regarding the most recent letter, "Whatever It Takes". I want to thank kingdommast, mb64, reannablue, the guest "TG", jojospn, shirleypositive72, ClassyMuse, SPNxBookworm, and girlinpink44 for their recent awesome reviews. And as usual, thanks to everyone who reads these! :) **

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ You were right. About everything, you know that? I was stupid and I let Ruby manipulate me into doing some really shady stuff. In fact my actions might be world ending, and the worst part is that she didn't have to do much to get me to start. I wanted to feel stronger and more capable. So I started drinking the demon blood basically as soon as she offered it to me. Sure, I told myself I hated it and that it was an unfortunate means to an end… But if I had really hated it that much I would have stopped. I was just lying to myself to make myself feel better. And the whole time I was lying to you too. I'm sorry Dean, I really am. _

_ I saw that letter you wrote when I was in the panic room… I probably shouldn't have read it, but when have I ever made the right choice? Anyway, you asked what happened to your little brother. I think I know. I bet you're expecting me to say he grew up, or grew colder, or just made friends with the wrong people. The truth is worse. It's that he never changed at all. He…Sorry. I chose to do all of this stuff because I'm not the innocent person you always see me as. I've got the potential to do some pretty bad things Dean. Yeah, I've got a nice IQ. But when it comes to common sense I'm not so sure I've got that. Not like you do anyway. _

_ You took one look at Ruby and you hated her automatically. You never stopped hating her, and the only times you ever let her work with us were after I told you she saved my life. And then I know you were doing it only out of some sense of moral obligation to me. But not because you liked her. Me? I let her in from the jump. Back before you went to Hell even… I used to tell myself I was using her to help save you, and that I'd kill her the second I got the chance. But I think it's pretty clear I lie to myself a lot when it's convenient. I flat out trusted her, and it was stupid of me. _

_ And when you said you'd rather I die human than die some kind of freakish monster? Well, I was surprisingly ok hearing that. I was grateful even… You were willing to risk hating yourself forever over my death just to prevent me from becoming something I would hate myself for. That's bigger than I think even you realize… And if you were to tell me now that it would be safer to end things than risk making the same mistakes again, I would listen. Because I trust your judgment. I've learned to trust it above all else, especially my own. Don't freak out. I know you wouldn't actually say that sort of thing right now. You're not one for suicide, and you sure wouldn't recommend it for me. It must be that "over-protective big brother complex" you've definitely got going on... _

_ By the way, I don't care anymore. I mean, I used to mind that you were always fussing and I used to want to fight it. Now I've learned I should appreciate it. Because the truth I'm only just fully realizing is that your little brother has a knack for making awful decisions. And the one thing that seems to stand between me and those bad choices is you. You have every right to want to be as far away from me as possible, and yet you still chose to let me back in. To trust me again, despite the fact I've given you nothing but reasons not to. I don't deserve your support after everything I did, but I won't deny I need it. So thanks, Dean, for being willing to fight for me and save me from myself. But most importantly, thanks for just being there still. After all, you were right. I'd rather be a flawed human with my brother any day.  
_

_Sam_

**Secondary Author's Note: Thanks for reading! I've got some awesome requests/idea coming up, but please feel free to give me more! And your reviews make my day, so please share your thoughts. :) **


	73. Please

**Author's Note:This letter is not a request. However, I just re-watched 7X10 "Death's Door" last night, and after I was done crying, I had to write a letter for it. Seriously, that episode is in my top three. It is both heart-warming and heart-breaking, and just so beautifully done... :'( Anyway, this letter was written by Dean to Bobby, while Bobby is in the hospital. I want to thank kingdommast, judyann, Leia 96, mb64, jojospn, SPNxBookworm, and girlinpink44 for their recent lovely reviews. And thanks to all who read these! :D  
**

**Disclaimer: I don't own Supernatural. **

_Bobby, _

_ We've had nothing but crap thrown our way for ninety nine percent of all our existences. You'd think we've earned a break, wouldn't you? Yet now we've got to take down the leviathan. And we will. I promise we will. But first you've got to do something for me. You've got to pull through this one, ok? You've been possessed, stabbed, electrocuted, and even died once before. This is one bullet. You can handle one little bullet because you're you. You can handle anything, right? _

_ See, I found my reason. You told me I needed to pull my head out of my ass and find a reason to keep fighting? Well you're it. Because I'll be damned if I'm just gonna sit by and watch that Dick get off easy after what he did to you. I was exaggerating when I said I didn't care if the world went off the cliff because it just wants to anyway. I mean, I stand by my belief that the world has certain suicidal tendencies… But I do still care. Because there are people in this world I still want to see have some peace in their lives. Namely, you and Sam._

_ You know I'd do just about anything to keep Sam safe and happy. But I want you to know I think you deserve the same. What? You really thought the protective caring stuff was just on your end? You've been looking out for me since I was a kid Bobby. Of course I care. God, I never really say that, do I? I mean we're men. No way do we hug and talk about our feelings, and that's fine by me. But I do wish I'd told you some of the big stuff at least once. _

_ Like how grateful I am that you came with Sam and me to try and kill Lilith the night I went to Hell. It sure wasn't going to be a fun trip, and you were totally risking your own neck by doing so. But you were there. And you were there when I got back, too. Yeah you tried to kill me at first, but I can't blame you for that. But when you figured out I was really me, you were just...there. I mean that in a good way. You were still surly and sarcastic as ever, and that was exactly what I needed. I needed that normalcy in order to feel ok, and you seemed to know it. You didn't press me to "talk about it", and you didn't act weird around me like I was fragile because of what I'd been through. You just treated me the same as ever, and it was great. _

_ But you've always been great at being there for me. Remember when I was twelve and I got my heart broken for the first time? Ok, that's me being over dramatic. I'd been "dating" that girl for all of a week and a half when she had to leave town because her summer at her grandparent's was over. I was still relatively innocent, so after she left it felt like my world was shattering. Sammy was too young to understand, so I didn't bother him with it. And dad was off on a hunt, so I couldn't bother him with it. But I was staying at your place and you were more than happy to talk to me._

_ You gave me possibly the worst speech about love anyone's ever been given, but it was still perfect. You told me, "Kid. Love is always gonna bite you in the ass eventually. What counts is whether or not both parties involved in a relationship decide they're masochistic enough to keep trying anyway. That's what marriage is for. Someday when you're old enough, you'll find a girl crazy enough to want to stick around. And you'll be crazy enough to want her to. And so even though there'll be down days and up days, you'll go through them together. Until then, just remember that you're young and you should be enjoying yourself, not moping around over some dumb girl." Like I said, it was a terrible speech. But it did the trick and cheered me up. Not to mention it's probably the most honest relationship advice I've ever been given… _

_ Course you've never been one for dishonesty. Well, I'm putting a disclaimer on that: The job doesn't count. But you know of all the people in my life, you're the only one who never lies to me. Maybe a few white lies here and there, but I mean you've never betrayed me. Sam has a list a mile long of times he's lied and cheated behind my back. Cas won the award for 'longest run keeping Dean fooled'. But you… You've always been straight forward with me. You've never manipulated or used me. You've just given me all of your support and asked for basically nothing in return… _

_ Damn it Bobby, why did this have to happen? Why you? I know you said you'd kill me if I died before you did, but that doesn't make it ok for you to just go ahead and die. It's not ok. You had better get through this. Just like you got through the not walking thing, and the Crowley having your soul thing… You're going to bounce back and help us take Dick Roman down. And believe me when I say that asshole's days are numbered. I'm going to kill him slowly and then dance on his freaking grave. But first you've gotta get better, ok? Because I don't think I can do this without you. You've been the best non-legally adoptive father a couple of damaged adult men like Sam and I could have dreamed of, and we still need you. So please just get through this one Bobby. Please. _

_Dean_

**Secondary Author's Note: Thanks for reading! Now that I've dealt with my Bobby related feels, I will get back to writing people's requests. I have many great ones in line, but please feel free to add to my list! :D And your reviews are so appreciated, you have no idea. :) **


	74. The Real Thing

**Author's Note: This letter is for ClassyMuse, who gave me a suggestion a while ago for an "angry letter to Chuck". Well I thought that sounded like fun today, so here it is! This letter is from Dean to Chuck, written shortly after 5X09 "The Real Ghostbusters". (The episode with the Supernatural convention...) I want to thank flygirl33, shirleypositive72, jojospn, mb64, Er-BearG32, ClassyMuse, judyann, twomoms, kingdommast, SPNxBookworm, and girlinpink44 for their recent awesome reviews. And thanks to everybody who has read these! **

**Disclaimer: I don't own Supernatural.  
**

_Chuck,_

_ I'm going to put this question to you in the simplest way I can think of… What the hell gives you the right, huh? Yeah, you're a prophet of the Lord or whatever. But these are our lives you're writing about man! You're actually documenting every painfully dark or awkward moment of our existences, and I'm completely not cool with that! Actually, you know what? It's not the writing part that bothers me. It's been useful once or twice to have the future down on paper… No, it's the selling it in fantasy book form that's really pissing me off. I don't remember Luke or John or whoever selling copies of their books and holding "Story of Jesus" conventions where people dressed up as the disciples and did fake Last Suppers! _

_ You weren't even going to tell us about those conventions, were you? If crazy Becky hadn't tricked us into showing up, you would have never breathed a word of it to us… You'd just have gotten to wander around behind our backs capitalizing on our shitty lives. How is that not supposed to creep me out? And what else have you not told us? Oh, right. There's the tiny matter of you not mentioning that some demon named Crowley had the Colt this whole time. Because really, who needs to know the location of the only weapon that might ice the devil that's trying to take over the world? That's not important at all… But I digress. _

_ Still, the thing that pisses me off the most is the way you cater to your fans by giving them VIP access to the worst moments of my life and Sam's. You know what I had to listen to at your little book club? I mean aside from the complete mockery of hunting in general… I had to listen to people quoting my brother and me for their own amusement. And I don't mean they were using our punch lines. You want to know the number of times I heard someone dressed like me tell "Sammy" that their dad had told him he might have to kill him? Seven. And that's about seven too many in my opinion. _

_ I know you're a prophet and you see all this crap happening, but I don't think you get it. Not really. The reality of it all is that it hurts, Chuck. When my dad told me I might have to kill my own brother, it damn near destroyed me. I was a wreck, and I came close to losing it so many times. Every day I had to live in fear that Sam would suddenly sprout horns or some crap, and that would be the day I'd have to kill him. And the worst part for me was my knowing I probably wouldn't be able to anyway. I knew that if it came down to it, the odds of me actually shooting Sam, even if he was a monster, were a million to one. So then I felt guilty for knowing I probably wouldn't do the right thing, AND guilty for knowing that if I did the "right thing" it would still be wrong, because I'd be killing my little brother… _

_ See, this is the stuff you touch on in those stupid books but never really grasp. You're just going off of how you think a person would feel in the situations you've seen in your weirdo visions. But those guesses don't hold a candle to the real thing. I've lived the real thing Chuck, and it sucks. Hell, I'm still living it. As I'm sure you're aware, I've got a giant pile of crap on my plate, so the last thing I need is to know there is a cult of 'fans' out there who spend their free time pretending to suffer in the same ways I've really suffered. _

_ My brother and I give everything for this stupid world, and ask for so little in return. But I am asking for…Not even asking. I am demanding our privacy, Chuck. No more books. Not a single one, you hear? You asked me what you do for a living…Well I don't really care as long as this isn't it. I suggest you find a job that doesn't involve selling the suffering of my brother and I in paperback form, or I swear I will make it MY job to hunt you down. And no arch angel will be enough to help you pull my foot out of how far up your ass I'll shove it. Got it? Good. _

_Dean_

**Secondary Author's Note: Thanks for reading! Have I mentioned how much I still love requests and reviews? Yeah, I totally still love them. ;) **


	75. That Night

**Author's Note: This letter is for kingdommast, who requested a letter from "Dean to Sam about the night of the fire." I thought that was a great idea, so here it is! This letter was written by Dean sometime shortly after 1X09 "Home", because in that episode Sam learns that Dean carried him out of the house the night of the fire. :) I want to thank kingdommast, ClassyMuse, Leia 96, SPNxBookworm, mb64, flygirl33, jojospn, judyann, twomoms, Lewlou15, and featherkitten for their recent awesome reviews. And thanks to all of you readers! :D**

**Disclaimer: I don't own Supernatural. **

_Sam,_

_ You told me you didn't know I'd carried you out of the house that night. The night Mom died… I guess I never really thought about it before, but you don't know much about what happened do you? I mean, Dad sure as hell doesn't talk about it and I'm not exactly fond of the topic myself. So I guess I just never thought about where that leaves you. You only know that Mom died, but you can't remember it, so you just don't think about it like me. Because when you do think about it, it isn't a memory. It's just an event like something out of a history book. And whatever emotions you feel are based on everything that came after. Not what happened in that moment. But for me it's different… _

_ I remember that it was an ordinary night. Mom and I had just put you to bed, and Dad came home from work just before I went to sleep myself. Mom tucked me in and sang to me. She sang "Hey Jude" just like she always did, and I fell asleep just like I always did. It was any old night in my normal, peaceful life. Until I woke up to lots of noise. I heard dad shout for mom, so I got out of bed to go find him. I wanted to check that everybody was ok… It seemed to be coming from your room, and as soon as I got to your door, he came running out of your nursery. And suddenly he was handing you over to me and telling me to get you outside as fast as I could. He looked so damn upset Sammy, it scared the crap out of me. One look in his eyes and I knew something was really wrong. I had never seen him look so horrified…I froze up for a second, because if Dad was freaking out then I knew I should be terrified. But then it hit me that I had a job to do._

_ So I held onto you and ran. Down the stairs, through the family room, out the front door… I didn't stop until I was on the lawn. And then I looked up at your nursery window and saw fire everywhere. It was so loud, which caught me off guard. I had never realized before that fire made noise, but this was a crackling, popping, roaring presence that attacked my ears and blocked out the rest of the world. The smoke was billowing out and across the yard. I wanted to run and cough, but I was too shocked to do anything so instead I just stood there dumbstruck. And it was so hot standing so close to the flames. It was the worst heat I had ever felt. And I was staring at the window looking for any sign that Mom and Dad were ok… Then suddenly Dad had me. He had us both, and he dragged us away just in time, because the window kind of exploded and the fire got even bigger._

_ That was the moment I knew. The window shattered, and so did my whole world. Because Dad came out of the house and grabbed us, but Mom wasn't with him. I somehow just knew that she wasn't coming out of the house. She was gone. For the rest of the night it was a long string of firemen and police officers and paramedics. And none of them knew what to do with me. Some of them tried to be cute. They talked baby talk to me and acted like nothing life altering had happened to me at all. I'm pretty sure they thought I was just some dumb toddler. Then there were those who looked at me with so much pity. That was even worse because I didn't want their pity. I wanted them to bring back my Mom. And then it was just over. Everyone left, and Dad took us to a local motel for the night. And I remember he cried, Sammy. I'd never seen him cry before. Hell, I don't think I've seen him cry more than twice since…But still never like he did that night. He was so completely broken, and there wasn't anything I could do…_

_ So yeah, it was basically the worst night of my life. Even though I didn't get burned, those flames seared the whole thing into my memory forever. I will never be able to forget the night my family was destroyed and my world was ruined. And now I'm sure you get why I don't talk about it a lot. But even so, you deserve to know the details I could give you. Besides, even with the trauma that night caused me, it also gave me something important. It gave me clarity. My whole world was just ripped apart, but I had one thing to hold onto and keep me going. I had you to look after. So even if you can't remember it all like I can, and you'll never be able to understand the way I feel whenever I remember those events… I still have to be grateful to you. You're the thing that kept me sane Sammy. The anchor I needed. I carried you out of that house, but you carried me through the days that came after. So thanks. _

_Dean _

**Secondary Author's Note: Thanks for reading! Have I mentioned how much I love requests and reviews? Well, I do love them. :) **


	76. Somewhere In The Middle

**Author's Note: This letter was actually requested by three different people, all at different times. Chlorine, GuestJ, and then Leia 96 all suggested a letter from Castiel to Meg. Chlorine was most specific, stating that it should take place shortly after 8X17 "Goodbye Stranger", thanking her for her help, and Castiel should not know she is dead. So, here it is! Castiel wrote this letter while on the lam at all those Biggersons. I want to thank reannablue, judyann, SPNxBookworm, kingdommast, writerofthelord, jojospn, mb64, CanadaLover008764, Lewlou15, twomoms, and CrazyLadyInVegas for their recent awesome reviews. And thanks to you amazing readers! :)**

**Disclaimer: I don't own Supernatural. **

_Meg,_

_ You asked me if I missed the days when the apocalypse was nigh. At first I thought the question was ridiculous. How could one miss the looming threat of the end of this world? But then you made a very good point. You summarized your reasoning by explaining that, during those days, you had been "bad" and I had been "good", and things were less complicated as a result. I don't know if your prior lack of morality is something I would consider desirable, but my own former sense of morality certainly is. _

_ I had a purpose back then. A clear set of goals, and although the challenges I would face along the way appeared insurmountable, I never felt guilt in my pursuit of success. I knew that if I were to aid Dean and Sam in the aversion of the End of Times, then no matter the personal cost, it was the right thing to do. And so I fought and bled and suffered, all for the achievement of this ludicrous goal. And in the end when we overcame our terrible odds, and stopped both Heaven and Hell…Well that victory filled me with such a feeling of power. Everyone we had met, yourself included, had informed us of our impending failure. Yet we still won. _

_ So a belief grew within me that I could do anything. I set about the foolish task of single handedly introducing all angels to the foreign concept of freedom of choice. It was absurd that I believed I was capable of erasing thousands of years of obedient instinct just by talking to them…But as you pointed out, back then I was different. I was innocent, and capable of harboring such faith in my brethren. But it was a downward spiral from there. The mistakes I have made since the end of the apocalypse are, for lack of a better word, embarrassing. I have not only committed terrible acts, but also professed my belief that they were good. All and all, I am filled with enough regret to make me long for those days during the battle against Satan and Michael. The days when I was better and my friends and I stood together against a dangerous future. Although I knew that my choices back then would most likely get me killed, at least I could still make them with a clear conscience. _

_ But this was not originally meant to be a letter in which I discussed all of my past mistakes. You are aware of most of my flawed decisions, and you even seem to find my new-found "bad" side endearing. This letter was actually meant to thank you. I haven't been able to search for you to thank you personally, since I am currently unable to focus on much more than the guardianship of a certain object. But I felt the need to express my gratitude for everything you did to help me. Yes, I am referring to recently when I needed to find that crypt and tablet, but I am also talking about the ways in which you have aided me in the past. I have not forgotten that it was you who stayed as my guardian while I was…indisposed, in that mental ward. It was you who chose to watch over a broken angel who would most likely cause you trouble at some point in the future. I appreciate it. _

_ You also asked me why it is that I am "sweet on you". Maybe it is because of this. The fact that you have been there for me through times when I was lost, and times when I needed help… But if I had to give my most honest answer, I think I would say it is as you said before. You are a little good now, and I am darker… We are meeting somewhere in the middle, coming from opposite ends of the spectrum. Together we are a confused shade of grey compared to the black and white behaviors our kinds are used to, and it just seems right. So until I see you again, thank you Meg. For everything. _

Clarence

**Secondary Author's Note: Thanks for reading! I want to point out that this was a Castiel letter NOT on a multiple of twenty. lol Yup, I am officially willing to write Castiel letters whenever. I have some Castiel suggestions that have been in line for a while, but for any of you who have been holding in your Castiel requests, feel free to let them fly now. Also, any kind of request is still welcome of course, and reviews are greatly appreciated! :D **


	77. Vacation

**Author's Note: This letter is for GuestJ, who request "a letter from one brother to the other giving reasons why they should take a vacation." I thought that was a fun idea, so here it is! A letter from Sam to Dean, shortly after 6X12 "Like A Virgin". First, I want to thank twomoms, kingdommast, jojospn, judyann, Lewlou15, GuestJ, CrazyLadyInVegas, SPNxBookworm, mb64, and girlinpink44 for their recent awesome reviews. And thanks to all who read these! **

**Message for GuestJ: I can't reply to your reviews for obvious reasons, but I wanted to thank you for having taken the time to review each new chapter after you got back from your trip. It was very sweet of you to leave a thoughtful message for each one, and I really appreciate the support! :)**

**Disclaimer: I don't own Supernatural.  
**

_Dean,_

_ So I've been trying to come up with a way to make these past six months up to you. And before you even start thinking it, I know you'll say I shouldn't feel guilty about stuff I did when I had no soul. But the thing is, now that I've got a soul I can't do that and you know it. I let you nearly get killed or worse too many times to just let myself off the hook. So although I can't go back in time and stop you from getting turned by that vampire, or look for you after you'd been taken by those fairies…(See, I'm not even laughing at that. That's how sorry I feel about all of this stuff.) What I can do is try and give you something you didn't have that whole time..._

_ Dean, I really think we should take a vacation. I'm not even joking at all. You've earned it man, that much I know. You put up with my jerk-self for six whole months. The least I can do now that I care is offer you a little down time. Think about it. We haven't just gone somewhere to simply relax in years. When was the last time we took time off for ourselves? It was like four years ago when we went to Los Angeles, and even then we ended up working a job. Wouldn't it be great to go do something random and fun? _

_ Like, we're in Ohio right? Well I heard there's this town next door in Indiana where they make the world's best Boston Crème pies. Yeah, you'd think that award would go to Boston but apparently not. And I swear it isn't that creepy town where we killed the pagan god scarecrow thing. That was Burketsville, and this is a place called Swanson. Not even on the same side of Indiana. The other good thing about this town is that there's a classic cars museum. No, I'm not trying to sell your baby. Just thought you'd find it interesting. _

_ But I don't really have my heart set on that at all. In fact it's completely dull compared to most of the options out there… I guess I'm thinking too small because I'm not used to planning vacations…Really there are a million places we could go. You know we've gone by the Grand Canyon more times than I can count, and yet we've never stopped there? We should go check it out. Be a couple of normal tourists for once… Or what about a place with a theme park? We've been to every state with a Six Flags, yet we've never actually been in a Six Flags. That's almost depressing. I hear they've got one in California with some of the craziest rides around. We could even do stuff in the states along the way... _

_ At this point I know you're thinking we don't have time for this kind of thing right now. In all honesty we probably don't. But you know what? We'll never have time Dean. Not unless we make it ourselves. The world is always going to be full of things to hunt and jobs to do. But that doesn't mean it's got to be on us twenty-four-seven to do them. _

_And I'll also admit that after everything that's happened over the past two years or so, I kind of just want us to have some time to…Well to just be brothers again. I miss that. Like back when we used to go places and find something fun to do after the job. We'd see a J-Hawks game or go to a concert… Only this time we wouldn't even have to think about hunting, or monsters, or saving the world again at all. We'd just be doing whatever normal-by societal-standards thing we were doing. So let's ditch the job, just for a week or so, and go do something we want to do. Like I said, you earned this and I owe it to you. So what do you say we go have some actual fun for a change? _

_Sam _

_P.S. If you still aren't convinced, how about this? I promise I won't even complain about the music on the drive there._

**Secondary Author's Note: Thanks for reading! I love reviews and requests, so please feel free to pile them on. lol :) **


	78. Really Being There With Me

**Author's Note: So after the most recent letter "Vacation" I had three people suggest a reply letter from Dean to Sammy after the boys did take a vacation. It was requested by mb64, twomoms, and kingdommast. I will also add that ClassyMuse told me about the theme park "Cedar Point" in Ohio, where the boys were located during the time Sam wrote the last letter. All and all, here is the response from Dean to Sam, after they took weekend trip to Cedar Point for fun. :) I want to thank SPNxBookworm, mb64, ClassyMuse, twomoms, Lewlou15, jojospn, judyann, girlinpink44, GuestJ, kingdommast, reannablue, and WomanOfLetters for their recent amazing reviews. And thanks to everyone who reads these!**

**Disclaimer: I don't own Supernatural. **

_Sammy,_

_ So as you know, I really wasn't feeling the whole vacation thing when you suggested it. We have so much on our plates right now and I just couldn't bring myself to give it all up and let it all drop to go do something random or average. Guess that's why I made you compromise on a simple, local activity. But now I've got to admit, I don't regret letting you drag my ass to Cedar Point for the weekend in the slightest. You were right. I needed some fun, and holy crap that was was great!_

_ I mean the rides were all awesome. But getting to see your face as we went over that first drop on the Millennium Force? That was priceless. You kept saying to 'go big first because then all the other stuff seems easy '… Yeah, well your plan worked. The Mean Streak was nothing after that sucker. But freaking enormous as it was, I wasn't even paying attention to the drop. I was watching you. Your eyes were so dilated and you got sheet-white pale…I swear I started wondering if you were gonna grab my hand or something. You know they snapped your picture at the bottom of that first drop, right? And guess who bought a souvenir copy of it! Yes I totally did. No way could I pass up such a golden opportunity to own an embarrassing photo of my little brother. _

_I think that was really why I wanted that picture. Not because it was embarrassing, though that's definitely a bonus... I like it because it isn't a picture of the guy who went to Hell, or worse, the guy whose soul was still stuck there. It's just a picture of my little brother. Doing something crazy, but the kind of crazy that society accepts and that won't ruin your life. Not to mention, it's been a long time since I've seen you show real fear over something Sammy. _

_I know that it sounds weird, but hear me out. The past six months you were about as tough as they come. You were damn good at hunting because you didn't flinch even in the face of certain death. But that was also awful to watch because it just reminded me of everything that was missing in you. It reminded me that you weren't scared because you couldn't feel scared, or anything else really. It was just further proof that you weren't really you. So seeing you freak out over one little giant roller coaster? It was just plain refreshing. _

_ But it goes even further than that. All the stuff we've seen and done over the past several years... well any sane person would say it's been downright terrifying. But the thing is that you never really got to show it. Even with your soul intact, you always had to put on a brave face because it's the job, and true fear isn't a luxury in our benefits package. So oddly enough, seeing you let go and be genuinely scared meant you were actually letting go of the job for that moment. It was really nice to see. _

_ So when you said you wanted to make up for my time with robo-you, and give me a fun break, and all that good stuff...you succeeded. But the biggest part was what you said last. You wanted us to have the chance to just be brothers again. And you know what? For that whole day we were. And it was great. I mean I spent the past six months miserable and worrying that I would never see my kid brother again. My real brother, you know? And then he came back and drags me to a theme park and screams like a little girl on the first ride we go on. Nothing could have made me happier Sammy. Not a thing in the world. So thank you. For caring enough to force me to take a break, and for really being there to take it with me. _

_Dean_

_P.S. Ok, so maybe I was a little unfair earlier. You didn't scream like a little girl. You screamed more like an over-sized bitch-man. (Yeah yeah, I'm a jerk. I know.)  
_

**Secondary Author's Note: Thanks for reading! More requests and reviews make me the happiest author ever. :D **


	79. Before It's Too Late

**Author's Note: This letter is for LoveIsAllYouNeed96, who gave me a very specific request: **

**"A letter from Bobby to John telling him about all of the memories he's missing out on. Weechesters. The letter could be more of a rant about he isn't acting like much of a father to them because he's never there. You could include some Sam and Dean fluff with Bobby telling John that Dean is becoming more and more protective over Sam." **

**Phew! I did my best to meet all the points in that request. :) So here it is. A letter from Bobby to John when Sam was about 5, and Dean was about 9. I also want to thank SPNxBookworm, kingdommast, ClassyMuse, girlinpink44, Er-BearG32, mb64, jojospn, judyann, GuestJ, and Lewlou15 for their recent amazing reviews. And thanks to everyone reading these!**

**Disclaimer: I don't own Supernatural.  
**

_John,_

_ So I'm starting to get tired of telling you all the things your boys are doing over a damn phone, you know that? Honestly, you ought to be here in person to see this stuff. They're growing up fast John, and you're moving too slow. I mean when you're an old man, if you're lucky enough to last that long in the life, what are you going to have to look back on? You've got two great boys, but you're not focusing on that. How're you going to remember their childhoods John? You gonna catalogue it based on hunts you were doing that day? _

_ "I remember Dean rode his first bike while I was in Tulsa taking out a vatala. I remember Sam got his first honors award when I was in Blue Ridge putting down a werewolf." That sounds like a pretty crappy way to remember their lives John. And yes, those events did recently happen while you were on those hunts. I didn't mention them during our last chat because you had to go so quickly…Lucky for you, I thought I'd write them down and share them anyway. _

_ So while you were out in Tulsa tackling that vatala, Dean decided he wanted to learn how to ride a two wheel bicycle. Of course that would be normal for a nine year old kid…If he'd done a bike with training wheels first. But Dean had never even touched a tricycle, let alone the old 70's cruiser I had lying around in the garage. Then again, when has something like that ever stopped Dean? He was smart about it because he didn't ask me first. Instead he just snuck out there, dragged the thing into the junk yard, and kept trying until it stuck. _

_ Of course, when he didn't come back inside after a half hour I got suspicious. So I went out there to look for him, and I found him with the knees out of his pants and all banged up, but riding that bike like a pro. The kid must've fallen twenty times by the look of him, but he never gave up. Reminded me of that phrase "fall off the horse, get right back on". He ain't a quitter, that's for sure. And he was so proud of himself he forgot to even look guilty. He just kept shouting "Look Uncle Bobby! I'm on two wheels!" I wanted to get angry that he hadn't asked before he started riding a rusted bike with no helmet… But I had to admit the kid had guts. So instead I bought him a soda and told him it was a job well done. _

_ And Dean isn't the only one who's been busy. While you were off killing that werewolf, Sam was getting honored at his school. Apparently not many five year olds know their entire multiplication tables. The other kids in his class were learning to count to ten, but Sam was showing his teacher how to multiply by tens. The poor girl didn't know what to do with him I don't think. She'd never seen a kid that bright. She talked to the principal, and during the monthly assembly they gave Sam an award for "exemplary dedication to education". I'm pretty sure they made up the whole thing just for him. Not to mention I am completely sure he's the only kindergartener to ever be given an award for anything more than congeniality. I mean most of the squirts at that school will never walk on that stage for an award of any kind, let alone so young and for something made up entirely for them because they're just that good. It was really something special John, and it is a damn shame you missed it. _

_ I'll tell you who didn't miss it though. Dean was there with his class watching, and he shouted so loud for Sam that his teacher had to tell him to quiet down. Then I could see him turning to all of his classmates telling them that it was his little brother on the stage. He was grinning ear to ear. Honestly, I think Dean was happier about the whole thing than Sam was, and that's really saying something considering Sam was positively glowing the whole week after that. _

_ But that's Dean. He watches over Sam like a hawk. Or a surprisingly masculine mother hen. I swear Sam is never going to have to worry about a thing as he grows up, because Dean would do anything for him. I've seen Dean punch a kid right in the gut for trying to mess with Sam on the playground. (Yes, I gave him a talking to for that. Although it was more about not getting caught than it was about letting bullies run the show…) But even with all the training and short-fuse temper to make him a menace to anyone who ticks him off, I've never seen him lose control with Sam. _

_ He might be stern with him from time to time, but I've never heard him yell at the kid. He's gentle with him. Like the other day Sam fell on the stairs and bruised his knee so he started crying. And then I saw the mighty Dean Winchester actually lean down and "kiss the booboo away". It made Sam stop bawling, and when the kid left the room Dean turned to me and said, "Don't you laugh about it Uncle Bobby. A guy can't make his little brother feel better? " And then he just walked off. Like I said, Dean would do anything for that boy. And you should be proud to have a son who's that good to his brother. Heck, you should be proud of both of them for all they do. Sam's a damn near Einstein, and Dean is tough as nails with a soft spot for only his family. You couldn't ask for better couple of kids John. I just hope you find time to spend with them before it's too late, and they're a couple of adults. _

_Bobby_

_P.S. Photos enclosed are of Dean on the two-wheeled rust-bucket and Sam posing with his ribbon. I got copies, so these are yours to keep. _

**Secondary Author's Note: Thanks for reading! I am loving all of the awesome requests I've got in line. Please throw more at me. And reviews are amazing, so don;t be shy! :D **


	80. Backing You Into The Corner

**Author's Note: This letter is for Er-Bear-G32 who requested a "letter from Sam to Dean regarding the whole fake voice-mail thing at the end of season 4". I personally hated hat the voicemail never got mentioned after that, so of course I loved the idea of writing a letter about it. :) Here it is! A letter from Sam to Dean, mid season-5, talking about the voicemail that apparently must never be mentioned. lol I want to thank mb64, jojospn, GuestJ, twomoms, LoveIsAllYouNeed96, kingdommast, girlinpink44, shirleypositive72, judyann, Lewlou15, flygirl33, and SPNxBookworm for their recent amazing reviews. And tank you so much to everyone who reads these! :)  
**

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ I've tried too many times to think of the best way to approach this subject with you, and I eventually concluded I'm never going to want to talk about it. Not really. I just can't bring myself to. Partly because I'm afraid of what you'll say and partly because I am aware of how much it will probably hurt you to be reminded of what I put you through. But I still need to talk about it, so __I'm using the communication method favored by cowards and writing to you instead of doing this you face to face. _

_Sorry, I'm not even explaining myself, am I? This is about the voicemail Dean. The one you left me after I beat you up in that Honeymoon Suite and ran after Ruby. You left me that message saying that I was a freak and a vampire. You told me dad had "always said you'd have to either save me or kill me"… And then you said you were done trying to save me. _

_Now I don't want you to think this letter is me being angry, or me demanding an explanation I don't deserve. I don't need to confront you about that voicemail because I don't blame you for having been that angry with me. __I want you to know that I understand I deserved to be told all of that and worse. I know that I was being awful, believe me. This letter is actually meant as an apology and a thank you. _

_First, I am sorry for having belittled all you gave up for me by going down the path I did. You mentioned when dad had said to save or kill me? I remember you fought so hard to save me. No one fought harder, not dad and definitely not me. You gave up sleep and sanity to keep me from going darkside. You did everything in your power to keep me from becoming a monster. God Dean, you sold your soul for me so I would have a chance to live on and lead a respectable life. _

_But I betrayed you in the worst way imaginable. After everything Azazel did to get that blood in me, I should have never touched the stuff again. I should have stayed clean to honor everything you had done for me. But I didn't. Instead I turned around and willingly followed the guidance of a demon instead of the brother who had never lead me astray. __I was too busy being self-righteous and telling you off for not trusting me to make my own decisions, to listen to what you actually had to say. Too busy yelling at you that you weren't as strong as me and that I was the only one who could kill Lilith and save the day. There is no denying that I needed to be knocked off my high horse. And that last part, when you said you were done trying to save me…It did the trick. That shook me right to my core Dean._

_ In the past, every time I had screwed up you had been there to kick me back into shape. Sometimes aggressively, and sometimes when I least wanted you to try. But much as I fought you on it, you had never stopped trying. And you had always saved me. To hear that you wouldn't try anymore…Well, for all my talk about being stronger than you and finally being mature enough to make my own choices, the thought of not having you to watch my back or catch me if I fell scared the crap out of me._

_And I'm sorry that I ever pushed you to the point where you needed to say any of those things to begin with. I know you, and I know that even as angry as you were with me, those were the last words you actually wanted to have to say. It hurt you to do it, but I backed you into the corner from which you made that call. And __even after all of that, you still showed up in that crypt and did your best to reach out to me. __I sure as hell _didn't_ deserve for you to back down on what you said to come to my rescue anyway...But you never really go as hard on me as I've earned, do you?_

___So here comes the part where I say thank you. I've taken your support for granted too many times Dean. I'm lucky that even after all the crap I've done wrong and all the times I've hurt you, the worst you've ever done to repay me is leave an angry voicemail with some threats you didn't follow through on, even though you probably should have. But it's not really luck, is it? It's just you. So thank you.  
_

_Sam_

**Secondary Author's Note: Thanks for reading! I love that I have made it to 80 letters, and that's all thanks to your wonderful requests! I really adore them and all of you. :) (Also, reviews are totally great. lol) **


	81. Something Very Important

**Author's Note: This letter idea was very popular, and was requested by SPNxBookworm, girlinpink44, mb64, judyann, GuestJ, and reannablue. In regards to my most recent letter "Backing You Into The Corner" (letter 80)...These lovely readers wanted a reply letter from Dean to Sam, and I thought that was probably a good idea, given the subject matter for the prior letter. :) Just a reminder, this couple of letters are meant to have happened around early/mid season 5. Before you read though, I want to thank SPNxBookworm, girlinpink44, kingdommast, jojospn, mb64, Roseros, judyann, Lewlou15, Er-BearG32, reannablue, the Guest "TG", and GuestJ for their recent reviews. And thanks so much to every one of you incredible readers!  
**

**Disclaimer: I don't own Supernatural **

_Sammy,_

_ You know when I was reading that letter, at first I actually thought you were going to tell me you were going to Stanford again? All that talk about "being reminded of what you put me through", that was the first thing that jumped to my mind. I thought you had some kind of a mental break and were getting ready to ditch the job just after I got you back, and it scared me. But then I got to what you were actually talking about and it scared me even more. To think you've gone for months now believing all of that…Just listen, ok? _

_ I'm going to start off by saying something very important, so please pay attention… I never said any of whatever that crap was you heard on that voicemail. I don't know if it was the angels or the demons, or freaking God himself, but someone messed with your phone Sam. Because I never said any of that. Not one word of it. I left you a voicemail, but that wasn't it at all. Do you think for an instant I would seriously threaten to kill you? I guess I joke about wanting to kick your ass all the time, and I know I got mad and told you never to come back if you walked out of that hotel room... But I mean, "I'd have to kill you or save you and I'm done saving you"? I wouldn't ever say something like that to you, and you've got to know it. Deep down you've got to know that you could beat me senseless and I would still find a way to forgive you. _

_ I've fought for you and looked out for you for as long as I can remember. I've cried, bled, and died for you. No way am I gonna try and kill you because of one fight over a skank and a drug addiction. Because when you bottom line it, that's what it was. You hooked up with a bitchy girl, and you took some drugs from her. Normal guys make mistakes like that too you know. True, normally demons aren't involved and it doesn't set Lucifer free to pillage the Earth...But I guess you just drew the short straw where consequences are concerned. Now that doesn't mean your scott free of responsibility. But it definitely means you're not a monster because of what you did. _

_All of this emo-kid crap you've been harboring over what you thought I said…You can throw it away. I won't deny I was pissed and upset after the Honeymoon Suite thing. But I was mostly just worried. I could see you were making the wrong call but I could also see you were determined to think it was right. I was scared I was losing my little brother to something I couldn't save him from and that was new for me. I mean even when you died in Cold Oak I had options to save you... _

_But hard as it was, I was never going to give up trying. I'm the older brother. It's my job to stick my nose in your business and do everything in my power to pick you up from whatever stupid mistake you've made. Because I have your back Sammy, and I always will. We can move forward and tackle this pile of crazy together like we always do. Think about it...Why else would someone mess with that voicemail? Obviously they wanted to open a rift between us because they believe we're dangerous as a pair. And you know what? They're right. So what do you say we give them hell from us? Combine our efforts, just like they're scared we will..._

_ And do y__ou want to know what was in the voicemail I actually left for you? I left you a message telling you that we were family. That no matter how bad things got, and no matter how messed up you started behaving, nothing was going to change the fact that you're my brother. I would do my best to have your back no matter what, even if it involved saving you from yourself. And I told you I was sorry in the message Sammy. I punched you too. I said things I shouldn't have. We both screwed up, and now we've got to clean up the mess we made. But at least we're doing it together. _  


_Dean_

**Secondary Author's Note: Thanks for reading! I am still loving your requests, and still very much open to more. And your reviews are all wonderful, so thank you thank you thank you! :D **


	82. Impromptu

**Author's Note: After the heaviness of the last two letters, I thought it was time to do something a bit lighter. This letter is for CanadaLover008764, who requested a letter from Cas to Dean giving "Castiel's thoughts on what happened when Dean took him to the club." (Episode 5X03 "Free To Be You And Me"). I thought this was a fun idea, so here it is! I also want to thank flygirl33, SPNxBookworm, judyann, reannablue, mb64, girlinpink44, anon, WomanOfLetters, jojospn, Er-BearG32, GuestJ, kingdommast, and Lewlou15 for their recent amazing reviews. And thanks to every one of you amazing readers!  
**

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ I am not an expert on human interaction, but I am relatively certain most humans do not usually pay one another for sexual acts. I was under the impression that there is typically a period of time spent on courtship before the actual fornicating occurs, and then it is cost-free for both parties involved. But I realize now that the place you took me was a place of, how did you put it? Daddy issues? Basically, it was a place filled with examples of humans that were not operating under normal psychological standards. I wish I had known this going in because I might have then spared that poor woman the sudden emotional outburst she endured. Yet overall I do not regret the events that transpired. _

_ They made us laugh. And for you, it was not the kind of hollow or false laugh which I have grown accustom to in recent days, but a full and genuine laugh that I honestly can't be sure I have ever heard. For me, just expressing such pleasant emotions was momentous. As I know you are well aware based on your consistent reminders for me to remove "the stick" from my vessel's anal cavity, I don't often do that. As an angel, it is hard to let go of the thousands of years of strict militaristic training that have molded me into a soldier who does not allow himself to experience emotions. But for the first time in far too long, I really smiled and even laughed, and it was great. _

_ I feel the more time I spend with you and your family, the more I begin to adopt habits and feelings that make it easier for me to operate efficiently amongst humankind. They make it easier for me to make the best of my inability to return to Heaven. I even picked up a few habits that allow me to find fun in the most intense situations. It is from you that I learned to use insults to make light of dangerous encounters._

_ Do you know how amazing it felt to look Raphael in the eye and call him "my little bitch"? In that moment I finally understood why you initiate verbal assaults on your opponents when confronting them. It is to mask the fear you feel during the encounter. I had long suspected this as a coping mechanism of yours, but never had the chance to personally experience its effectiveness. When I looked at him and berated him with my words, I was able to calm the nerves I felt upon hearing his threat to kill me in the future. I felt empowered, despite my inferior abilities when compared to Raphael, and I enjoyed that feeling. _

_ Overall what I am trying to say here is that I was not anticipating doing anything last night, other than to sit and silently await the confrontation with my brother. I certainly was not expecting to partake in the visitation of a brothel, or the teasing of my much more powerful sibling. But despite the fact that your taking me to meet with Chastity and my insulting Raphael were impromptu events, I am still glad that these things happened. It was a great learning experience, to say the least. And even though you said that I am "not that fun", you also said you had experienced more fun with me than you had in a long time. I just wanted to inform you that particular part was mutual, so thank you._

_Castiel_

**Secondary Author's Note: Thanks for reading! I am so grateful to all of you reviewers and request givers, you have no idea. You make this series happen, so feel free to keep it up! :D**


	83. Just Not You

**Author's Note: So I was going to let the voicemail letters drop after Dean's reply letter...But then I got two requests (one from a new guest reviewer "anon", and one from the wonderful jojospn) for a reply to THAT letter from Sam. At that point, I simply had to. ;) So here is Sam's reply to Dean's letter "Something Very Important" (letter 81). I want to thank SPNxBookworm, judyann, WomanOfLetters, jojospn, mb64, kingdommast, Angel of Nightfall, and GuestJ for their fantastic reviews. And thanks to each and every reader!**

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ Before I say anything else, I have to say this… Stanford, really? After all the crap we've been through in the past year alone, and yet that was the first thing that jumped to your mind... I would find it funny if I didn't feel so bad about how much that clearly impacted you…But that really isn't what's important right now. I know I said I believed I deserved to be told all of those things from the voicemail I heard. And I guess I still think I do... But that doesn't mean I'm not incredibly relieved __to have figured out that voicemail was a fake. That you never said them. _

_I mean yeah, at first I found it hard to believe you weren't just trying to make me feel better or something. But then I had to stop and realize…The only reason I thought you might be trying to comfort me with lies is because you are always the one trying to comfort me. And that fact in and of itself was enough to make me fully believe everything you wrote in that letter. After all, you're right._

_ You really have "cried, bled, and died" for me. You've been my guardian since before I could talk, and you have sacrificed so much more for me than anyone else on this planet. Deep down I do know that who you are…My big brother, my best friend, and the person in the world most loyal to me…You would never threaten to kill me. That's just not you. And if I was acting more like myself when I listened to that voicemail, I would have known that. But I wasn't. _

_ I was basically high, for one thing. But that's a bad excuse. More importantly I was trying so hard to retreat in my mind from the part of me that knew what I was about to do was wrong that I was going through the motions almost as a different man to avoid the guilt. And it was that guilt that blinded me. _

_I was the one who felt like a monster. _Me_. So when I heard your voice saying it, I allowed myself to believe it was how you felt because part of me _wanted_ to be scolded for what I was doing. When I heard that voicemail, I wasn't in the right state of mind to recognize how un-Dean the whole thing was. Instead it struck me in such a vulnerable place, and it actually spurred me to commit to what I was doing. Because what was the point of stopping if I had already lost you for good? __But now that my head is cleared more, I can see what I should have recognized from the moment I left that hotel room. I hadn't lost you at all. _

_In all my life, you have never once abandoned me. Not when I left for Stanford. Not when dad told you that I was dangerous and might need to be killed. Not even when I was already dead, and you should have been free of the responsibility of me. So no, you wouldn't have cut the chord over Ruby or the demon blood. The Dean I know would get pissed, and probably punch me in the face…But then he would tell me to come back to him. He'd give me his trademark kind-of-embarrassed-to-be-sharing-his-feelings-but -still-determined-to-get-the-point-across speech about the fact that I'm his family, and that he isn't going to give up on me no matter how stupid I'm being. He would have even apologized._

_ Funny thing is, I can see from your letter that's exactly what you apparently did. And that just serves to reaffirm my belief in what you told me from the start of your letter. You never said any of those things. That voicemail I heard was a fake. And I can let go of the hurt and guilt. And you're right about the other thing too. When I think about it, whoever screwed with that message must have been doing it to try and pull us apart. And they were smart to try given how dangerous we are as a team. But they failed. We're still a team, and we'll handle this together. And really, that's all thanks to you. _

_Sam _

**Secondary Authors Note: Thanks for reading! I must ask that no one request that Dean reply to this letter, because I think it would be over-kill. lol However, any other requests you might have are completely welcome! And I adore reading your reviews, so please do share your thoughts. :) Also, kingdommast pointed out to me recently that this series now has over 700 reviews. I can remember when I thought 50 was the biggest thing ever, and now I don't even have the words...You are all so amazing, and thanks again! :D  
**


	84. Exterior Vs Interior

**Author's Note: This letter is for mb64, who requested "a letter from Crowley to both guys in any time frame, explaining why he sort of likes them". I haven't done a Crowley letter yet, so this totally jumped out at me. :) Here it is! This letter was written by Crowley, sometime mid to late season 7. I want to thank SPNxBookworm, mb64, kingdommast, Lewlou15, jojospn, judyann, kirkanalo, anon, GirlCapsicleInTheHouse2358, CrazyLadyInVegas, CanadaLover008764, and girlinpink44 for their awesome recent reviews. And thanks to everyone reading these! :) **

**Disclaimer: I don't own Supernatural. **

_Moose and Squirrel,_

_ It seems I've found myself in yet another predicament where I am forced to take your side. It isn't easy for a fellow as intelligent, powerful, and remarkably handsome as myself to admit he needs the assistance of two bumbling fools such as the likes of you. However, that really isn't the case, is it? See, I've finally come to the conclusion that the cover of your particular book is quite misleading. You wrap yourselves in cheap clothes right out of a lumberjack catalogue, drown yourselves in floor level liquor, and then top it all off with witless bravado. But that's only the exterior. It's the inside that holds the secret to your unbelievable success thus far. _

_ I'll start with squirrel. Your attic is clearly littered with daddy issues, codependency, and alcoholism. You lack a college education and your track record for emotional stability is nothing to brag about. Altogether, this is not the heroic image you would expect of the kind of man who stops apocalypses and saves lives for a...Well we can't really call it a living, can we? But I digress... Anyway, I stress once more that the image lies. Somehow, underneath this damaged, drunken, and appallingly dense shell there resides a small but vital stash of competence and (forgive how cliché this next statement is) courage. Yes, your unending dedication to hopeless causes is actually an important part of your skill set. Not to mention you surprise everyone with your unexpected ingenuity. Without these traits, you would honestly be useless to me. But these qualities have seen you through more impossible situations than any other human, save for your enormous brother, thus making them invaluable during times like these. _

_ And Moose… I feel that my assessment of your exterior must be more literal than that of your sibling's. You have the size, stature, and furry coating of a giant. You're like Hagrid, only younger and slightly narrower. Needless to say, you present the outward appearance of a slow and lumbering troll. But yet again, the diamond is in the rough. You are actually far from slow, in every sense of the word. You, unlike your loud-mouthed counterpart, did attend college at least for a while. And an IV League school at that… You are clever. A skill that trumps brawn any day. But luckily enough, you have that too. You are well trained, quick to strike, and handle pain like a true masochist. The Jolly Green everyone sees is actually a deadly, albeit highly psychologically unstable, assassin. The sappy eyes distract your enemies from the threat they actually face. It's really quite a trick… _

_ I guess over-all, if you were to ask me two years ago what allies I would want in the fight against this arrogant Dick, I would never have imagined you'd both make the cut. But alas, those were different times. Times when I was not yet aware of the valuable characteristics existing just below your charmless covers. But then again, nobody ever saw my own rein in Hell coming. I was, as one of you so eloquently put it before, a simple "punk-ass cross-roads demon". No one thought anything more of me. And then one day I captured the crown. I guess that's why I've grown to like you. And by like, I mean accept that I have a current use for you which allows you both to keep breathing. You are similar to me. You are both a mix of deadly cunning and durability hidden under an apparently harmless coating, only not __as literally as is my case. So for now, it seems that I will place my 'allegiance' with you. Just don't muck it all up, would you?_

_Crowley _

**Secondary Author's Note: Thanks for reading! I welcome reviews and requests with open arms. They can make themselves at home here. lol **


	85. Watch Your Back

**Author's Note: This letter was never requested, but I got in a mood and this sort of just happened. This letter is from (obviously very angry) Dean to Dick Roman, a couple weeks after 7X10 "Death's Door". I want to thank flygirl33, jojospn, Leia 96, girlinpink44, reannablue, mb64, Lewlou15, judyann, SPNxBookworm, kjdw, and kingdommast for their recent awesome reviews. And thanks to every one of you who reads these! :D  
**

**Disclaimer: I don't own Supernatural. **

_Dick,_

_I want you to know that you may as well have just signed your own death certificate. He might have died, but he spent his last moments giving us information. Intel I know I'll find a way to use against you, because I'm gonna screw you into the ground so far you'll roast in the molten core of the Earth. I'm not dumb enough to tell you what he found, but I can tell you that you aren't climbing out of the pit you just dug yourself. By the time I'm through, you will be nothing more than a quivering blob of pathetic tears. And then I'll finally let you die. Slowly. You don't get it do you? I mean I've seen all kinds of stupid, but you may just take the cake. Because you thought killing Bobby would make us weaker. You thought it would break us, even.  
_

_How about I tell you the happy little story of the last jackasses who hurt my family and lived to tell the tale? Oh wait, there aren't any because they're all dead. Azazel? He killed our mother but we paid him back appropriately. It might have taken us a good couple decades to find a way to finish him, but in the end I shot that bastard right in the head. I watched the life literally leave his eyes. Didn't matter that it had taken most of my life to reach that moment...It was just as satisfying as I'd always dreamed. Fast-forward a couple years and Lilith is the demon bitch everyone cowers from. Don't mess with her, she'll mess you up…blah blah blah. Well she did get me good. Sent my soul straight to Hell after letting her hulked out demon dogs rip me apart in front of Sam. _

_But you know what? Sam swore revenge and killed her sorry ass less than a year later. Sure, he almost destroyed himself in the process. But hey, that's what we do. We go and go until we can't go any longer, and then we find a way to keep going on anyhow. Because no one messes with our family and gets away with it. Zachariah just _attempted_ to kill my brother, and I still stabbed him in his ugly face. Lucifer killed Bobby and Cas, then tried to kill me…Sam locked his ass up in Hell for all of eternity. That Eve bitch tried to get us to kill Bobby…We ganked her slimy ass too. It wasn't easy. We had to go back in time to get the only weapon that could do it. But we succeeded. Because we always succeed.  
_

_Because we always have motivation. Yeah, there's the world to worry about. And we do care about that...But nothing motivates us like family. If you mess with our family, we kill you. It' that simple. It doesn't matter how long it takes us or how impossible the odds seem. It doesn't matter if you think you're indestructible. We find you and destroy you. So I hope you're good and scared Dick. And if you're not, then all the better for us you arrogant sonofabitch. Those who underestimate us always get the worst of it in the end. You think you're special? You think that out of everything we've hunted and killed, you're the exception to the rule? No. You're nothing new. Different shell and different skill-set. Same old pile of soon-to-be-dead meat. You're living on borrowed time and I mean it. So watch your back, because we're coming for you next._

_Dean_

**Secondary Author's Note: Thanks for reading! I still love requests and will get back to writing them straight away. I also love reviews, so please do share your thoughts! :) **


	86. Balthazar

**SPOILER ALERT!: Even the A/N contains spoilers for late season 6 content. CanadaLover008764, I know you aren't this far into the show yet, so please skip this one! ;) **

**Now that I got that out of the way... **

**Author's Note: This letter is for SPNxBookworm, who requested "a letter from Cas to Balthazar? He ultimately does kill his own 'brother' right? Maybe Cas feels really guilty and wishes he could take it all back." I thought it was a pretty deep request, and so I decided to write it. :) Here it is, a letter from Castiel to Balthazar written sometime while Castiel is in Purgatory. Don't ask me where he got the paper because honestly, I couldn't say. lol I know there was a problem with the website a few days ago regarding posting reviews, so to any who tried to review and could not do so, thank you still! ;) I also want to thank kingdommast, SPNxBookworm, judyann, Lewlou15, mb64, jojospn, WomanOfLetters, and Er-BearG32 for their recent reviews. And thanks to everyone who reads these! :D  
**

**Disclaimer: I don't own Supernatural. **

_Balthazar,_

_I have no words to express my remorse. The phrase "I'm sorry" is hardly suitable to cover my feelings regarding what I did to you...The atrocities I committed in Heaven and on Earth had all seemed an endless blur of suffering inflicted by my own hand. But none of them stood out in particular. Not really. I think that was my subconscious defense against the full force of guilt I would experience. I didn't want to face the extent of the pain I could feel in response to my actions. But that defense wore down over time. I tried to maintain it by letting my mind go in an attempt to be at peace with my sins. I took my friend's mental illness on myself in an act of penance and desperation. But even my voluntarily induced madness was not enough to distract me from my past forever. And over a year later it finally hit me. Here in this endless wasteland of monsters and bloodshed, in the place I realize now that I belong in, I faced the truth. I didn't just slaughter angles and humans. I didn't just play God. I also killed you in cold blood._

_You. My companion who, despite your interesting lifestyle choices, had never once done anything to harm me. You had fled the chaos in Heaven, wanting nothing to do with the war that raged upstairs. And yet upon my request you rejoined the fight to aid me. Simply because, though you never demonstrated your affections openly, we were friends. Brothers in arms. And you would honor that bond, so you stood by my side. Fought and risked your own neck under my continuous orders. You were honest with me always. You gave up your hard-earned personal stash of destructive weapons for my benefit. You even told me when Sam and Dean came to you behind my back. You did everything in your power to help me, and yet I betrayed you in the end. Worse than the manner in which I betrayed Dean and Sam, because at least their lives were spared._

_____But I did not spare your life. And w_hen I killed you, I was as stiff and empty as Raphael. As any angel ever was. You told me once that I was the inspiration for your choice to seek freedom. To fake your demise and escape to the Earth to live as you pleased. I was, at one time, the symbol of freewill and emotion. Rebellion and feeling._ And yet at the end I was as ruthless and cold as the angels I fought to destroy. All of my freewill and feeling was not enough to save me from making such a mistake. _And though I told myself it was not a mistake...That it was for the greater good, and that my plans were important, and that I needed to obey a higher power...The power of the cause…I see now that I was wrong. When I killed you I marked my fate. It was the first choice of many terrible ones that would lead me to the place I am now. I wish I could take it back. I wish I could restore you to health, my old friend. For even though you were always the most ornery of angels, you were also the most loyal to me, deep inside. And I repaid that loyalty with murder.

_I wish for you to know that I am ensuring I won't do anything like that again. I am not giving myself the chance. After I assist Dean in escaping this place we are in, I plan to stay behind. To trap myself here in Purgatory for all of eternity, or for however long I last before something manages to kill me. Honestly, it is what I deserve. I have proven that for all my talk of freewill, I do not possess the sense to use it wisely. Therefore I am a danger to everything and everyone I encounter. Unlike you, I cannot be trusted. And so I will trap myself in a place where the only things I can come in contact with are monsters like myself. I will miss Dean like I miss you still. But at least I learned from my past aberrations, and shall die at peace with my own damnation. I only wish you were alive to know it.  
_

_Castiel_

**Secondary Author's Note: Thanks for reading! I know this one was kind of dark, so hopefully the next one will be less sad. lol Anyway, I still appreciate requests and reviews immensely, so fire away! :D **


	87. My Little Sammy

**Author's Note: So after the recent kind of downer letter, I had some people suggest a happier letter was in order. I couldn't agree more, so I went through my list of requests trying to find a sweet one. This one jumped out at me. A long time ago, mb64 requested a letter "from Mary to baby Sam that's been put away for him to read when he grows up". I thought that had potential to be cute, so here it is! This was written by Mary when Sam was about five months old. I want to thank SPNxBookworm, jojospn, mb64, judyann, kingdommast, Leia 96, girlinpink44, and Lewlou15 for their recent supportive reviews. And thanks to everybody reading these! :D **

**Disclaimer: I don't own Supernatural.**

_My Little Sammy,_

_ By the time you actually read this, I suspect you won't be so little anymore. But that doesn't mean you won't still be little Sammy to me. That's because as your mother, it's my right to never see you as grown. Anyway, I got to thinking recently as I was filling out your baby book that those books are meant for you to look back on later. To see how you grew up, and get the information from your youngest years that you won't be able to remember on your own. Yet as I was filling it out I noticed it didn't allow for much detail. It gives a space for what your first word is, when you first sat up…All good things to know. But it doesn't give room for you to get a sense of your life as a baby. So I decided to take on an additional project. I'm going to write you letters each month. Share with you the stories of how you grew up and include the little details those baby books don't give me room for. _

_ First I thought I would tell you about your favorite foods. It's interesting, because it changes depending on who is feeding you. For example, if I'm giving you lunch, you like pureed corn. You will eat that yellow goop like there is no tomorrow. Well, eat it for the most part. A fair amount ends up on your face and bib… But that never bothers you. You are content to wear half your meal and enjoy the rest. If your dad is giving you food…Well you normally put up a fuss with him because you know he's a pushover. He can't stand seeing you make your unhappy puppy face, so if he offers you squished squash and you just refuse to eat it, he caves easily and gets you something you like better. But your true favorite food isn't even one food at all. It's anything Dean is giving you. _

_ I was hesitant at first to let a four year old boy try and feed a baby. Especially a messy eater like yourself. I was pretty certain I would end up scrubbing baby food off the ceiling or something… But if anything, I found that you eat more carefully for Dean. You don't make a mess and you don't spit things you don't like back at him. Several times I've tried to get you to eat your pureed green beans and ended up washing them out of my hair later. But Dean? All he has to do is tell you "clear landing for the airplane", and you open wide. I've had to work to not let myself allow Dean to feed you all the time, because honestly it's so much easier when he does it. Half the time you don't even spill. I swear you're trying to make it easy for him. _

_ And speaking of making things easy…You make bath time easy for everybody. Allow me to first explain that your brother was a menace when it came to baths. He hated them and wanted nothing to do with the tub. When he was a baby he would cry, but as he got older, it became less about tears and more about hiding. I would have to track him down, and then chase him once I found him. It took him until three to finally start liking baths, and that was only after I bought him a scuba-diving batman figurine to play with in the water. I was expecting to have the same trouble with you, but it was the complete opposite. _

_ You seemed to love the water. The first time I put you in the baby tub you got these big eyes. You looked like the coolest thing in the world had just happened, and you were too amazed to process it. But by the end of the bath, you were nothing but giggles and smiles. By now you've even figured out you can splash me. Though that probably has to do with Dean… He splashed me once when helping me and that was the start of the end. I swear you picked up on it. You watched him just that one time, and not a bath has passed since where you haven't waved your arms around and turned me into a dripping mess. Still, I guess I can't complain that you follow your brother's lead. _

_ When I first told Dean he was going to have a brother I was worried he would react badly. It wasn't that he was a generally jealous kid or anything…I just knew some children get upset at the idea of a new sibling. But Dean had just the opposite reaction. He was excited and wanted to be a part of all the preparations. He helped your dad set up your crib. He helped me pick out your mobile. He proudly announced to his entire preschool class that he was getting a baby brother. And then the day came when I actually had you. Dean came into the hospital room and saw you for the first time, and his eyes were just so full of awe. Your dad helped him hold you, and he just stared at you like you were the biggest treasure he'd ever seen. I knew right then and there that all my initial worrying had been pointless. There was no way Dean was going to feel jealous or upset. He was going to watch over you and be the most dedicated big brother you could ask for. _

_ I guess that's all the stuff I can think of for this letter. I know it isn't much, but you are only five months old, after all. But I hear babies make leaps and bounds after they reach six months old, so the next letter should be full of all sorts of stories. And there are still so many months after that. So I hope you enjoyed reading this first one, and I hope it gave you a better feel for your babyhood than the baby books do. Until next month…_

_Much Love,_

_Mom_

**Secondary Author's Note: Thanks for reading! I am loving the requests I have in line, but I can always use more, so please feel free to make suggestions! And reviews are totally appreciated immensely. :) **


	88. Perks

**Author's Note: This letter is for GuestJ. A while ago GuestJ requested a letter from a scared Dean to either Sam, Bobby, or Lilith written some time during the infamous 4X06 "Yellow Fever". GuestJ, you said you knew I liked a challenge, and I sure do! :) I chose to write from Dean to Sam. Dean wrote this (while trying to control his ever mounting paranoia and terror) sometime while in the motel but while Sam was out working to save him. I want to thank jojospn, SPNxBookworm, Lewlou15, mb64, ClassyMuse, flygirl33, twomoms, Leia 96, judyann, and kingdommast for their recent incredible reviews and support. And thanks to all you epic readers! :D **

**Disclaimer: I don't own Supernatural. **

_Sammy,_

_ You know, I've got just this one day left and I spent half of it wandering around aimlessly in fear of everything until a friggin' yorkie scared me home. Which totally sucked man. But I guess that was better than what I'm doing now, which is sitting in a room alone and even more afraid of everything. But I'm off topic here… So before the developing fear I have that my pen is going to slip out of my hands and stab me in the leg gets the better of me, I have some things I need to say. _

_ First, I'm sorry I ran off today. I acted like it didn't matter to me that I'm going to die in…well now it's just a few hours… Oh God that just made my pen wobble. Anyway, I just up and left you but I should have stayed. Because that's not the first time I left you after a show of "I can't be bothered to care" like that. Last time my head was on the chopping block, I spent the better part of my last year alive pretending to not care if I died. When you needed me most, I checked out and became Mr. death can bite me for all I care. Because I knew it could bite me, literally. And that scared the crap out of me. And so instead of being there for you and allowing myself to hope we could fix things, I "left". And you were on your own in the fight to save me. I shouldn't have put you through that, and I'm sorry. And I just did it again, didn't I? Guess it's a habit. I get scared for my life and I just leave. Act like I don't give two craps. You've called me out on this before, but I just wanted you to hear me admit I'm sorry for doing it to you. _

_ And secondly, before I left I yelled at you a bunch of crap about how sucky our lives are. And they do suck most of the time. Case and point being me, right now, awaiting my death for the second time in less than a year. But that doesn't mean they always suck. I mean I have a lot of good memories of our lives too you know. Yeah, you and I barely tolerate the endless drives together most of the time. And you've gotta hate my repetitive playlist of music accompanied by my off-key singing-alonging… But it all means that we also get to spend a lot of time together. Plenty of brothers don't really get that. Most live on opposite sides of the country and barely ever speak. So sure we're stuck in a car too many hours of every day, but it's better than not knowing each other at all. At least to me it is. _

_ Remember a while back when that Djiin got a hold of me? I told you it showed me my life if mom had still been around. Or, well I guess it was how I thought life might have been, but that's not important. What I am trying to get at is that in that dream world, you weren't my brother. I mean we were related. But we just weren't close. I told you that too, but I never told you how much it actually bothered me. I saw in that world a version of you that had a great life. And I was happy for that Sam, I really was. But I also hated that when he looked at me, he was only ever angry, pitying, or concerned for my mental health. There were no inside jokes, and no nick-names he hated but tolerated because I was saying them. There wasn't any kind of connection at all. And it was just depressing Sammy. So yeah, our lives are crap. But I'd rather face the crap all day than face a white-picket-fence life without my brother. _

_ Finally, this is the second time you have fought to save me from certain death. And like we both know, I act tough like I'm not scared. (Ok. So I screamed at the top of my lungs because of a cat… But that WAS scary! And if you say otherwise and I live past this evening…I will pound your face in.) Anyway, what I'm saying is that I really AM scared. But I'm also confident that you'll try literally everything you can to help me. You always do. So if I had to pick a plan to try and get out of the mess I'm in, I'm going to say this plan is the best one I could ask for. I trust you to either pull through, or have had literally no way to stop it. It's one of the perks that comes with having a brother you actually get along with. Or at least with having a Sammy. So thanks for trying. I just really hope you succeed. _

_Dean_

_P.S. I just broke the motel's clock. It was ticking menacingly at me this whole time and I needed to make it shut up. _

**Secondary Author's Note: Thanks for reading! I do love requests, and like GuestJ said, I enjoy a challenge too! ;) Please send your ideas my way! And reviews are very much appreciated. :D **


	89. Old Time Sake

**Author's note: This letter is for ****LoveIsAllYouNeed96**, who suggested "A letter from Bobby to John set in season 7 telling him about what the boys have achieved over the years and how proud he is of his boys. You could include something like Bobby promising John that he'd look after the boys." I thought this was a super idea, and so here it is! Bobby wrote this some times during the first episode of season 7. There are a couple little spoilers for season 6 if you aren't through that whole season yet. I want to thankCanadaLover008764, jojospn, ClassyMuse, SPNxBookworm, girlinpink44, A Reader, judyann, mb64, GuestJ, Lewlou15, kingdommast, twomoms, and WomanOfLetters for their recent amazing reviews. And thanks to all of you who read these! :D  


**Disclaimer: I don't own Supernatural. **

_John,_

_ I found a letter from you today. Obviously it was from a long time ago, when the boys were about nine and thirteen I'd guess…You were pissed about me letting them do stuff that wasn't related to hunting. But then again, you always were butting heads with me about that. We used to have some pretty loud arguments about it, didn't we? You were always so convinced I "treated them like babies"…Worrying all the time that they wouldn't turn out as strong as you'd like. I just thought I'd say that you never needed to worry. They turned out great John, really they did.  
_

_ I've never met better hunters, and I've met most hunters out there. Sam…That boy just doesn't give up. I've seen him face down the Devil himself and come out ok. Damaged, sure. What hunter isn't? But he's functioning. Even after ungodly lengths of time trapped in Hell with Lucifer playing dungeon master, that kid bounced back. And he didn't come out of it and leave the life either. He came back from it and immediately got to work fixing this broken world. It impressed the crap out of me John. I'm telling you, there never was a more determined man, let alone a hunter. _

_ And Dean? You do know that boy has been to Hell too, right? Went for selling his soul to save his brother. Damn fool move, but I have to say I respected him for it. That man would do anything for his family, and unlike ninety percent of the guys who say that about themselves, Dean isn't all talk. And when he came back from the pit, he had his dark moments just like Sam. Times when he looked like it was all too much…But he never caved. Not even when the world was ending and he had been told there was absolutely no way to stop it. He just kept going. Clung on to his family and was motivated by whatever hope he had left of protecting them, and by god, he did it. When the world was sure to end, he saved it.  
_

_ I'm telling you John, they both turned out tougher and full of more "give-em-hell" than anybody I've known. And keep in mind, I've known you too. You were always one hell of a fighter. You were legendary in the hunting community. You were the great John Winchester, invincible and menacing as they come. And your boys took up that position after you were gone. I doubt there's a hunter around who hasn't heard of them. And anyone at a high enough pay grade knows that they've killed Azazel, and Lilith, and defeated Lucifer and Michael, and the Mother of All, and are threat number one on Crowley's list... They've taken down things plenty of hunters have never even heard of.  
_

_ So no, I didn't always make them practice with their shotguns or grapple with knives. But I don't think it mattered at all. They grew up strong and tough and as damn dedicated to saving people and knocking monster heads as anyone could have dreamed of. Even more so I think. And honestly, I think that's just because it's who they are. Your boys are good men through and through. __You were always fussing and saying they shouldn't be coddled because they needed to be ready to face the life of a hunter… _Well they face each day not just like hunters, but like heroes. They're real heroes John. And I know you told me in the past that they weren't my boys, and you've got me there. I ain't they're biological daddy. But I'll say this much. If I were, I'd be the proudest father around. And as it stands, I'm the proudest not-father in the world. I promise I'll look after them John.  


_Bobby _

___P.S. For old time sake... Yes, I do mean I'll make sure they get their down time. Lord knows they've earned a break every now and again and YOU know I will always be happy to give it to them.  
_

**Secondary Author's Note: Thanks for reading! I still appreciate requests, so please share your ideas! :) And your reviews have all been so wonderful, I always look forward to reading them! :D **

**To a couple of guests whom I couldn't reply to via PM for obvious reasons:  
**

**GuestJ: Again, thank you so much for reviewing every chapter when you got back. It meant a lot to me! I hope you had a great vacation, and I wanted to tell you that I ADORE your recent request. ;) **

**A Reader: Thank you thank you thank you! I am so flattered that you think I managed to convey the fluctuating relationship between the brothers with this series. I am so flattered, I barely have words. :) Also, your request was really great! I love the parallels you pointed out, and am more than willing to write a letter highlighting them! **

**WomanOfLetters: Really cute request! It's totally on my list. :) **


	90. Marathon

**This letter is for a guest named "A Reader", who left me a really well thought out request for "a letter from Sam to Kevin. How Sam knows what it's like to dedicate your entire life to getting into college, and then having that ripped away from you because of your "destiny", how he knows what it's like to lose a girlfriend, etc." I loved the parallels this person drew between Kevin and Sam, and so of course had to do the letter. :) So here it is. It is written sometime during or just after episode 8X14 "Trial and Error". I want to thank kingdommast, kirkanlo, LoveIsAllYouNeed96, jojospn, GuestJ, mb64, A Guest, twomoms, SPNxBookworm, and Lewlou15 for their recent awesome reviews. And thanks to all who read these! **

**Disclaimer: I don't own Supernatural. **

_Kevin,_

_ Ok man, so I know I told you the other day that saving the world is a marathon and not a sprint, but I want you to understand why the advice is valid. I'm not just throwing words around to sound helpful. I know this from personal experience. Actually, looking at you today I see a lot of myself in your situation. You know I became a hunter because my dad raised Dean and me into the life... But did you know that I actually got out for a while and went to college? And did you know I had a girlfriend there who I loved and that she was killed by a demon? Like I said, I look at you now and kind of see me back then…_

_ When I was young all I ever wanted was to get away from the hunting lifestyle and go to a good college. I used to stay up all night sometimes studying for tests to make sure I got straight A's. I had dreams of becoming a lawyer, and I actually got into Stanford on a full-ride and practically aced my LSAT… I was all set up to live the life of my dreams. I even had this amazing girlfriend. Her name was Jessica Moore… She was smart, and funny, and stunning. I was going to ask her to marry me, and I was going to have everything I'd ever wanted. Until the demon got involved._

_ There came this time when Dean needed my help with something, and I had to leave for the weekend to go with him. I left Jessica, and our apartment, and my perfectly normal life for all of two days, and that was when everything fell apart. When I came back I found Jessica pinned to our ceiling and bleeding from a wound in her stomach before she was burned alive. She looked terrified. I swear I will never forget the pain and fear in her eyes just before the fire erupted around her. And then the whole room went up in flames, and Dean barely got me out alive. But Jessica didn't make it. I watched her die at the hands of a demon, and the worst part was that it was all because of me. It was because the demon was manipulating me. When something like that happens…_

_Well it makes you feel like you just want to do whatever it takes to fix everything. To fight with everything in you to get back to that place you'd had before whatever crap hit the fan. But first you've got to realize that, although there is a light at the end of the tunnel and you DO stand a chance of having a demon-free existence…It is never going to be exactly like what you lost. You won't be able to go back to the moment before it all happened and just start over from there like you never left. The sooner you realize that the road ahead can lead to a good place, but it will be a different place, the better off you'll be. _

_And then you need to recognize the best way to navigate that road. __The thing is Kevin, running yourself into the ground doesn't fix anything. You want to stop the demons? You want to get your life back on track? You need to be in the right shape to do it. If you aren't then the world won't get saved. And maybe even more importantly, if you kill yourself from overexertion, YOU will never get that happy ending you're working toward. If you want to say screw the world and why should you get stuck saving it, that's fine. But fight for you. You didn't deserve whatever happened to you. And you have every right to get some sense of normalcy back, so work toward that._

_ But you've got to take better care of yourself along the way. Like I said, you are a priority. I know how easy it is to put the job before your health. I've gone nights without sleeping because the research seemed more crucial at the time. I've watched my brother live off of greasy foods and alcohol for too many years because he lets the job use him up and by the time it's done, he doesn't have the energy left in him to think about cholesterol or his liver. But I'm telling you right now…Get into the habit of having the energy. You can't live off hot-dogs and you can't keep going on virtually no sleep. You need nutrition and rest, and an actual break every now and again. You need to look out for your health. It's the only way you're going to make it to the finish line. _

_ I've been running this race for about a decade Kevin, and I've learned to pace myself. Sometimes you think you're on the verge of finally fixing everything, and that's when everything blows up in your face. If you've already burned out your motor you won't stand a chance against the new wave of problems… So please, Kevin. Take better care of yourself. Believe it or not, I'm not just saying this because we need your help to save the world. _

_ I'm saying this because, as I pointed out, I see a lot of similarities between us. I understand when you say it hurt to watch Crowley break Channing's neck, and I understand what it's like to have a normal life planned out for yourself that you have been working on forever, then to have it destroyed in a single moment because of some destiny you never wanted…It's awful. And it really sucks just seeing that happen to someone else after it already happened to me. But the least I can do is to offer you some advice gained from years of experience in this area. Extra years that hopefully you'll never have to go through. So I repeat…It's a marathon Kevin, not a sprint. Take it one step at a time and you will get there. We both will. _

_Sam_

**Secondary Author's Note: Thanks for reading! I've got some more great requests in line, but I'm always looking for new ones too. :) And I welcome each and every review with open arms. lol **


	91. You Knew Her Name

**Author's Note: This letter was requested by** **kingdommast and Er-BearG32. Both of these lovely readers wanted a reply letter from Kevin to Sam regarding the most recent letter, "Marathon". I thought that sounded like a good idea, so here it is! I want to take a moment and thank SPNxBookworm, kingdommast, jojospn, Lewlou15, Er-BearG32, mb64, GuestJ, twomoms, CrazyLadyInVegas, girlinpink44, and judyann for their recent amazing reviews. And thanks again to all who read these! **

**Disclaimer: I don't own Supernatural. **

_Sam,_

_ You knew her name. I didn't think you'd know her by name because you didn't know her at all except the night she died. So I guess that got my attention more than anything else you wrote…Not that I didn't pay attention to the rest of it, but I have to say that meant the most to me because it proved you actually care about all the people who don't come out of this ok. For a while there I'll admit I wasn't sure. It's not that you seem like a bad guy, but you and your brother just seem to attract a lot of death…I figured you both must be past the point of caring about the names of all the victims. But I was wrong, because you knew Channing's name. _

_ I'm sorry you've had to deal with everything you've gone through, especially Jessica. She sounds like she was really nice. I suppose I've assumed this whole time that you and Dean are ok with all of this because you guys are the experts. It was dumb to make that assumption because I never chose to get stuck with being a prophet and yet I'm considered an expert on all these tablets. But it never really occurred to me to question what got you into this life or if you would want to get out of it too. And I definitely never saw you as a college guy. No offense. I mean you're smart and I know you could handle the research, but it's hard to picture you ever stressing out about mid-terms when I've seen you dealing with bigger issues, like sabotaging human slaughterhouses to prevent the end of humanity…But even you were normal once. And then you weren't anymore. _

_ You were right when you said having all your normalcy ripped away makes you feel like you'd do anything to go back to how things were before. You know what I was doing the night my whole world imploded? I was freaking out about my SAT. I was so convinced that I needed a perfect score, and in that moment I couldn't see how anything could possibly matter more than acing the test. I was on the phone with Channing and she was trying to calm me down. She told me that no matter how hard it was to imagine it at the time, one day college wouldn't matter anymore. Looking at my life now, I'm definitely not missing the irony. __But now I want college to matter again. I want to go back to having panic attacks about my grades because the worst thing that could possibly happen would be getting a 790 instead of an 800 on a section of my SAT. Because then if I'm terrified of failure, at least failing wouldn't mean dying or getting my spine ripped out through my nose. _

_Basically, I want to have a future again. So I'm going to try my best to take your advice. You're telling me that you've been at this for ten years, and the only way you've survived all that time is by learning to pace yourself? Then I guess it's worth a shot. __And believe me, I really hope I don't get stuck doing this for another eight years or more…But what you're saying makes sense. If I'm ever going to make it back to normalcy, I can't kill myself in the process. And I do want to make it there. I feel like crap about my situation, but I'm not actually to the point yet where I don't care about life anymore. And it's good to know you're not thinking like that either. If you can last ten whole years of this and still have hope that things will get better, then I can believe I've got it in me to hold out too._

_ By the way, I appreciate that you care enough to even be giving me advice at all. Ever since I became a prophet it's been one long string of people needing things from me. You guys needed me to help with the Leviathan tablet, then Dick Roman wanted me, and Crowley, and now I'm back with you. It's definitely better with you guys, I'm not complaining about that. I'm just saying it feels like I don't really have a life at all anymore and no one cares. I know you and Dean both care that I don't die, but I don't have much support outside the area of just staying alive. So thanks for showing me you're thinking about my life and not just my current occupation. _

_ And do you want my advice? Take your own. Pace yourself with these trials, because reading these tablets…Let's just say God writes like he has a majorly sadistic side, and I don't get the feeling he'll make these easy on you. So take care of yourself too, and then we can both get to that finish line eventually. _

_Kevin_

**Secondary Author's Note: Thanks for reading! I really appreciate every review left, so please share your thoughts. Also, I am loving these requests you are all coming up with. Please keep them coming! :) **


	92. Peculiar

**Author's Note: This letter was requested by ClassyMuse, who wanted me to write a letter from Castiel to Lucifer. I thought that was a smashing idea, and so here it is! This was written by Castiel for Lucifer just after the season 5 finale episode "Swan Song". Like, literally within twenty four hours of those events. And now I want to thank kingdommast, Er-BearG32, flygirl33, CrazyLadyInVegas, applepieisnice, twomoms, GuestJ, jojospn, mb64, SPNxBookworm, Lia Whyteleafe, and Leia 96 for their recent amazing reviews. And thanks to everyone who reads these! :D **

**Disclaimer: I don't own Supernatural. **

_Lucifer,_

_You called me a "peculiar thing" when we met and I have since then come to realize how right you were. I am unlike the other angels, yourself included. I might have rebelled as you once did, but my motives were not as yours were. I didn't choose to fall because I wouldn't bow to humanity. I fell because I wanted to see humanity rise. I rebelled for them, not against them. You said that humans were flawed, and they are. They blunder and stumble and sometimes even break their world. But as a good friend once told me, most humans do try to be decent. There are those who choose to stand up once more and fix whatever is broken. To make amends for their mistakes. And I believe this is why God instructed us to bow to them. They are better than we are._

_After all, when do angels ever admit they were wrong? Angels are even more willing to destroy in the name of their cause than humans are, and even when faced with blatant proof they're making poor choices, they will not back down. They're self-righteous, cold and calculating. The only emotions they outwardly demonstrate are wrathful ones. But humans act from their hearts. Their feelings, good or bad, drive everything they do. And this impulsive lifestyle does not always end well for them, but it's much better than living a life where all decisions are pre-made based on strict orders. The humans take responsibility for their actions. _

_And these humans you call lesser, they forgive one another for their faults. When you and Michael had your differences you deemed it reasonable to tear apart the entirety of all worlds in an effort to defeat each other. When Sam became addicted to demon blood, Dean was clearly furious. But he overcame that rage and found it within himself to open up to his brother once more. You and Michael have never shown such magnanimity. No angel has. But humans…_

_Sam is proof enough that humans can be better. He let you out of your cage as a result of terrible choices, but when all seemed lost, that man…A mere flawed human…Gave everything he had to make right his mistakes. He was willing to sacrifice not only his life, but his afterlife as well to protect a planet full of people whom most of which would never know he had even existed. And his brother is proof as well. Even when it seemed inevitable that you and Michael would fight, and that Sam would never again escape the confines of his own mind, but instead die on the field of battle...Dean still chose to go to that cemetery and be with his brother. He wouldn't let his brother die alone, even if it meant he himself would die an awful death as well. So t__here is a selflessness and loyalty in humans that angels do not comprehend. They__ will put others first, and not just other humans. Dean and Sam have both risked themselves for me in the past. Dean says it is because to them, I am like family. And if I have learned nothing else from my time with the Winchesters, I have at least learned that family is the strongest and most valued bond humans can share. And they willingly extend this connection to include me. Because humans, for all their flaws, are capable of generosity beyond that of any angel._

_So yes, I rebelled against the will of Heaven. I stood and sacrificed my own life for a handful of humans I believed were capable of saving all worlds. For my family. And I do not regret that choice. As Sam and Dean have taught me, just the few you call family are worth the blood and pain of the fight to protect them. But angels, for all their talk of "brothers and sisters" will never understand family like humans do... Except for me. And no doubt, many angels consider me foolish. But I think it is just as__ you said...I am peculiar. And perhaps it is peculiarity that Heaven now needs most. _

_Castiel_

**Secondary Author's Note: Thanks for reading! Loving the reviews and requests, so please keep em' comin'! ;) **


	93. What You Did For Me

**WARNING: Spoilers for season 7 contained even in the A/N! Spoilers for 7X03 "The Girl Next Door" and 7X13 "The Slice Girls" to be exact... **

**Now that that's cleared up...**

**Author's Note: This letter is for shirleypositive72 who said to me a while back, "What about a letter from Dean to Emma (his Amazon daughter)? Or Sam to Dean after Sam killed her? Or Emma to Dean? Or Dean to Sam after he killed her? I'm felling the Amazon theme." I thought this seemed like an interesting challenge, and so here it is! I selected to write the letter from Sam to Dean, and it takes place within twenty four hours of the Emma incident. I want to thank twomoms, Lewlou15, SPNxBookworm, girlinpink44, GuestJ, kingdommast, judyann, mb64, and jojospn for their recent awesome reviews. And thanks to each and every reader! :D **

**Disclaimer: I don't own Supernatural. **

_Dean,_

_ I was so pissed at you after Amy. I kept being angry that you didn't trust my judgment and that you were keeping secrets from me…And yeah, that you'd killed my friend. But I think I understand now why you did it. Because it's the same reason I pulled the trigger on Emma. I saw you standing there facing a monster that had the potential to kill you without thinking twice. A creature who I didn't know, and had no reason to trust, and it was wrapping you around its finger. And so I did what any hunter worth their salt would do… I killed the monster. _

_ And that's all she was to me. A monster. She wasn't your kid, or my niece, or even an innocent girl who couldn't help at all what she was... She was just a threat to people in general, and most importantly, a threat to your well-being. And I couldn't risk letting her walk, or even taking her with us and trying to help her. Especially when you were vulnerable around her because there was an emotional element that couldn't be avoided. I could never have forgiven myself if I had faltered and not fired, and you had ended up dead later. All because I wouldn't shoulder the burden of being the one to shoot her and take whatever blame you later put on me. _

_ And that's exactly what you did for me with Amy. You knew that if I ever found out about you killing her I would definitely be furious and feel betrayed, but you did it anyway because you could see the bigger picture when I refused to see reason. Amy was killing for her son yes, but she was still killing people. And if she ever decided that I was a threat, or even just useful as a meal, she would probably have no trouble killing me too. You ended her life her to keep me safe even when you knew it risked me hating you for it. You would rather have me alive and pissed at you than dead because you wouldn't do the right thing. And in the moment when I saw Emma holding that blade, I could finally understand why you had done what you did. And if you could be that selfless for me, I was definitely going to repay the favor. _

_ Only it didn't really turn out the same, did it? I know you've got to be upset about Emma, but you still haven't chosen to be upset at me. No matter how many times I tell you that she wasn't really yours, you continue to blame yourself before anyone else. I know you, and you won't let yourself off the hook that easily. You'll keep telling yourself she was your responsibility and you let her down. That's just who you are. You've always been too good at beating yourself up over things you had no control over or no way to see coming… _

_ But grateful as I am to have a brother who will blame himself before he gets mad at me…I'm not convinced he should. It's not healthy to keep doing that to yourself Dean. So I'm going to offer you this advice: Get mad at me anyway. Save yourself from the grief, and at least pretend you're pissed off at me. Yell it out, tell me I hurt you, anything you need to do to convince yourself it was on me. And then we'll work past it like we always do. It's easier that way. We fight a lot more often than most people I think…But we also make up every single time. _

_ When you killed Amy, I took all my frustration and anger out on you. The anger that she had been born a monster, the frustration that she had made the mistake of killing people…Even my own embarrassment that I had allowed my feelings to cloud my judgment. I threw it all on you for a long time. Now it's my turn to let you dish out some anger on me. If it'll be therapeutic for you, then I'm more than willing to do it. So please, Dean, let me carry that burden for a little while. You don't deserve to carry it yourself, and I really don't mind. After all, it's what a good brother does. It's what you did for me. _

_Sam _

**Secondary Author's Note: Thanks for reading! Please do keep the requests coming, and I love all feedback, so don't be shy! I'd love to read whatever you have to say in a review. :D **


	94. Not Like You Are

**Author's Note: This letter is for mb64 and a Guest who both requested a reply letter from Dean to Sam in regards to the most recent letter, "What You Did For Me". I thought "Why not?" and so here it is! :D This is Dean's response, written still within the first day or so after the Emma incident. I want to thank mb64, kingdommast, a Guest, jojospn, shirleypositive72, LewLou15, another Guest, yet another Guest, SPNxBookworm, reannablue, and GuestJ for their recent lovely reviews. And thanks to everyone who reads these! :D **

**Disclaimer: I don't own Supernatural. **

_Sam,_

_ I appreciate the offer, I really do. But there's a good reason I'm not taking out all my Emma-related crap on you… It's the same reason you're no longer mad at me about Amy. You say you're not griping at me anymore because you understand my motives? Well seeing as they're the same as mine were, I understand yours too. What you did, you did to help me. You were protecting me from dying at the hands of my own daughter. And yeah, I stand by the fact that she really was my kid. DNA doesn't lie, even the screwed up Amazonian kind. Still, me being her father or not didn't matter to her. She would have killed me no matter our blood relation. Actually, she'd only have done it specifically _because_ of our blood relation… But you get my point. _

_ And when push came to shove, and I wasn't going to be able to kill her, you stepped in and you stopped me from ending up an extremity-less mess on the floor and wearing some seriously emasculating chest art… And I'm grateful Sammy, I really am. You were willing to bear the burden of taking her out because I was worth it to you. And I know you. You go on and on about how you worry I torment myself because of Emma's death, but I know you're feeling guilty about having shot your own niece._

_ You weren't in the moment. In that moment, like you said, she was a monster to you and nothing more. But when it was all said and done I know the guilt crept in. You're Sammy, and that means you'll let me off the hook immediately, but I know that at the back of your mind you're thinking that she was your family too…You are such a hypocrite. Well I'm giving you the advice you'd originally given me: Let it go. It was the right thing to do, and it wasn't your fault she was a monster who needed to be put down. _

_ Because you know what? You were right. Not about her not being my kid, but about her not "being mine"…Does that make any sense? What I mean is that she was our blood, but blood doesn't always make for family. Remember dear old Grandpa Campbell? He was such a charming relative. Honestly, how we ever survived so long without his compassion and guidance is beyond me… Really though, we both know that guy was a serious jackass and bastard, and he deserved what he got after everything he put us through. No matter how closely related to us he was, it didn't matter to him. He chose to betray his own grandchildren and hand them over to the King of Hell. He made his choice, and we weren't it. _

_ Emma, she was no different. She had the option to not kill me. She knew she did because she fed me a long bullshit story of how she wanted me to protect her and give her a chance at normalcy because I was her father and she trusted me… It was all lies and instead of trying to get out of the Amazon gang, she chose to kill me anyway, all the while with a smile on her face. She was my daughter, but she wasn't my family. Not like you are. _

_ So even though I'm still trying to wrap my head around having brought a kid into the world accidentally only to end up having watched her get shot just a few days later…I'm not going to cope with it all by yelling at you about it, and I'm sure as hell not blaming you. You did what needed to be done and you did it for me. No matter the cost to you. That's what real family is for. You have proven time and time again that you would suffer and even die for me. You would spill that blood that binds us without a second though if it meant saving my ass… And I would do the same for you. That's family in its truest sense. It's what Emma never really was to me, but what you have always been. So thanks. _

_Dean _

**Secondary Author's Note: Thanks for reading! My birthday is tomorrow, so I may or may not have time to post a letter. If not, there will definitely be one either Saturday or Sunday! :) Also, please feel free to keep the reviews and requests coming guys! Especially the requests, which are the fuel for this whole operation. ;) **


	95. The Worst Thing

**Author's Note: This letter is for reannablue. A little while ago she asked me if I could write a letter about the humor and trauma of what Sam went through with the clowns during 7X14 "Plucky Pennywhistle's Magical Menagerie". I definitely liked that idea, so here it is! Dean wrote this within forty eight hours of that episode. I want to thank kingdommast, mb64, a Guest, ImpalaLove, Lewlou15, jojospn, GuestJ, another Guest, and SPNxBookworm for their recent amazing reviews! And thanks to all you wonderful readers! Oh, and a quick thank you to everyone who sent me birthday wishes. They were greatly appreciated! :) **

**Disclaimer: I don't own Supernatural. **

_Sammy,_

_ You know, I'm familiar with all the feelings I go through on hunts…There's adrenaline during the chase. Pain when the bad guy flings me around. Dread when I realize something nasty is coming your way and I have to haul ass because one of our phones is out and I can't just warn you properly…(That happens way too often and you know it.) Probably the one I know best is the fear that I might not make it in time and you'll suffer for it. But this time there was a new fear thrown into the mix. _

_ I had to be scared the bad guy would manage to kill you _and_ that you would die in the worst way you could imagine…That you would suffer a fate more awful than any you had faced the possibility of before…You might actually die at the hands of an evil clown. And though writing "evil clown" makes me want to laugh, it's partly just a cover for my guilt. _

_See, I'm always scared you'll die. And believe me when I say I'm always scared it'll be painful for you too… I guess that's just part of the whole "being a big brother" package. Then you add in the fact that we're both hunters who face legitimately dangerous crap on a daily basis, and all that fear gets kicked into a kind of overdrive that is entirely uncontrollable. But the worst thing I could possibly imagine would be for you not just to die, but to die genuinely scared._

_ I've seen you face certain death before and not even flinch. You might have your head on the chopping block, but you always just looked determined or brave the whole time. Now, it's never a good moment whenever I've thought you were totally screwed, but at least you never looked really frightened. I admit I've never been able to handle seeing you look terrified of anything. When you were pre-school age and you needed a nightlight, I always had to plug one in for you at every motel. It didn't matter that it was hard to sleep with the glow, because I couldn't bear to see those freaking puppy dog eyes you've got go wide with fear. Not when I knew I could do something to help it…_

_ So the whole time I was trying to stop that witch, I kept seeing in my head this picture of some giant malicious clown stabbing you in the gut, and your eyes just looked so petrified…And those eyes also looked accusing. Because I know deep down that I protected you from all the scary stuff in the world except that one thing. I stuck you at Plucky's all the time and didn't pay attention to how much you hated it. I didn't listen when you complained about the clowns. I didn't have to be bothered by your scared face because I wasn't even there to see it. __I dropped you in the middle of clown-land and just left you there._ I ignored the thing you were actually most scared of, and instead fed the fear. _So basically, when that psychotic nerd-witch told me he'd sent sadistic clowns after you, I was just as terrified as you. Not just that I might lose you, but that I might lose you to something you hated so much…That you would die in real fear and it would be completely my fault._

_Sam, when I tease you about being scared of clowns I don't actually find it very funny. Ok, I admit I totally do for about a minute…But the humor is short-lived and then I remember the reason for your fear, and that I scarred you for life. And I know you've got enough to deal with right now with the whole fragile psychological wall situation you're facing. (Yet another thing I'm not proud of being responsible for.) And you shouldn't have to be worried about killer clowns too. So, even though it's a little late coming, I'm sorry Sammy. I should have helped you grow out of that fear, but I didn't. I just helped it grow period. I'm just glad you lived through your encounter. _

_Dean _

_P.S. I might feel bad about the clowns, but I do NOT feel guilty about laughing my ass off every time I see you still have glitter in your hair. I mean your sideburns actually sparkle, Sam. They freaking sparkle!_

**Secondary Author's Note: Thanks for reading! I love reviews, so please do share your thoughts. And I still enjoy accepting suggestions for letters! :) **


	96. Someone I Could Always Trust

**Author's Note: This letter was written in response to Er-BearG32's request for a letter from "Sam to Bobby, before he jumps into Lucifer's Cage in "Swan Song" (either as a final goodbye or just final words to him)". I loved this idea, and therefore went ahead and wrote it up! So this letter was written by Sam for Bobby the night before the season 5 finale "Swan Song". It would basically have been written right after the very first letter in this series, "Everything", which was from Sam to Dean. Anyway, I want to thank jojospn, GuestJ, Lewlou15, reannablue, mb64, kingdommast, a Guest, and SPNxBookworm for their recent lovely reviews. And thanks to all who read these still! :D**

**Disclaimer: I don't own Supernatural. **

_Bobby,_

_ I wrote one of these for Dean earlier and I thought it was hard because I had no idea what to say. But I suppose this whole process is generally a hard one because I know what I want to say for this and it's still difficult to write it. I guess I'll start with the biggest thing I need you to know... Other than Dean, you have been the most important member of my family for so many years. You have been an amazing friend, mentor, and so much like a father to me that it's hard to remember we aren't actually biologically related. I have always been able to count on you no matter how bad things got. _

_ I want to thank you for having stuck by me after you found out about the demon blood. I'm sorry you ever had to hear me screaming from inside that panic room, but the fact that you were willing to go through it just to save me from myself only serves to further prove how good you've always been to me. And even after I messed up again and let Lucifer out of the box, you refused to give up on me. You know, when that demon possessed you and made you tell me you never wanted to see me again it hurt more than when Dean was mad at me even... I mean I knew I'd done a lot of terrible things, and I knew that I deserved your anger and probably worse. But to actually hear it was still painful. _

_ Because I've always looked up to you. I've always been honored that you respected me and trusted me, and I was so ashamed to have lost that respect and trust. I don't think I can put into words how relieved I was when you told me that you hadn't been calling the shots at that moment. That you still wanted me around, and that you'd have my back no matter how many mistakes I made. It was the encouragement I needed to really set myself straight. I knew I couldn't let you down like that again. Especially when you were so willing to forgive me…_

_ But you've always been that way with me, haven't you? I still remember when I was five years old and Dean and I were staying at your place for Halloween. I was dressed up as a Jedi and had that little plastic light saber I kept swinging around? You told me to stop swinging it because I'd break something, and like a good five year old would, I completely ignored you. And ten minutes later I'd swung that plastic tube right into a pile of books you'd been going through the night before. They had all been book-marked for research and I totally destroyed hours of work you'd put into organizing them. The force of the impact knocked me over, and I sat there on the floor kind of in shock from what I'd just done…_

_ You heard the noise and came rushing into the room, but instead of yelling at me, you did something that totally surprised me. You came right up to me and asked me if I'd been hurt. No shouting and no rage. Just concern. It wasn't something I was particularly used to getting coming from anyone other than Dean, and that was maybe the first time I knew I could really trust you. Not just trust you like, be comfortable staying at your house, but trust you in the same way I trusted Dean. It was the first time I knew you were genuinely family to me. _

_ Of course, after you figured out I was ok you immediately told me to "clean up my mess"… But I was more than willing to. I knew I'd done something wrong, and I was just grateful you gave me the chance to fix it instead of shouting at me. And things really haven't changed much, have they? You still haven't yelled at me about Ruby, or Lucifer, or any of it. You were worried about me first, and after you figured out I was ok, you told me to do my best to clean up the mess I've made. You've even helped me to do it. You've sacrificed a lot this year alone to help me. And it means so much Bobby, it really does...  
_

_ So this is me, cleaning up the pile of books I knocked over…Doing my best to make up for my mistakes. And I'm grateful you've been there to have taught me how to do it. Thank you Bobby, for being someone who looked out for me and cared about me through all the craziness we've been through. Thanks for being like a father to Dean and I. And thank you for being someone I could always trust. I won't forget everything you've done for me. _

_Love,_

_Sam_

_P.S. Please look after Dean for me. If he does what I asked him to do and leaves the life, help make sure he gets to keep whatever new one he builds for himself. And please remember look after yourself too. I know you won't leave the life, but still want you to live a long one for me. _

**Secondary Author's Note: Thanks for reading! Loving the requests and reviews guys. You are all amazing! :) **


	97. Some Words

**Author's Note: This letter is really just for fun. GuestJ gave me this really unique reuest a little while ago: "How about an apology letter that Dean has to write to another student (Dean's victim) while he's serving a detention for defending Sam. Dean knows his family is leaving town soon so, he doesn't write the kind of letter the teacher expected." I simply couldn't say no to that because it was just too cool! :D So here it is...I imagine Dean was about ten when he wrote this. I also want to thank Er-BearG32, Lewlou15, jojospn, mb64, and GuestJ for their recent reviews. You guys are the best! And thanks to all of you who still read these! You are also amazing! :D **

**Disclaimer: I don't own Supernatural. **

_Dear Russell Thompson,_

_ I owe you an apology for what I did to you earlier today. Like literally, I've been told I need to apologize. The teacher says it was wrong of me to hurt you and that I shouldn't have punched you in the face at all, let alone all three of the times that I did. I shouldn't have thrown you on the ground to do it either… And I also shouldn't have made certain to break your nose, because violence is never the answer…As Mrs. Timbers said, talking things out with each other is always much better. That's why she told me to write this. So I could apologize and also "express my negative feelings in a more constructive way". And I guess I think she's right. I mean verbal abuse is always so much better, isn't it? After all, that's what you used when you picked on Sammy… _

_ You shoved my little brother and called him a freak, and just that one moment was simple enough to get all the other stupid kids shoving and teasing him too. And it made him cry. He's only a six year old after all... Now I won't stand by and watch my little brother get bullied. But you know that now, don't you? That's kind of why you're sitting in the nurse's office right now with tissues shoved up your nose…But like I said, I like Mrs. Timbers' advice. I think it's a better way to get even with you. So how about I use some words that will make you cry? _

_ How about "hippopotamus"? I know you're probably not smart enough to read such a big word, so let me explain for you what it means…A hippopotamus is a giant dirty animal that lives in Africa. It does pretty much nothing but eat all day, and it smells worse than a backed-up toilet. It's fat and it has no life. And nobody even cares about it when they go to the zoo. Zoos don't even have them, that's how boring and gross they are. And that was the first thing I thought of when I saw you. I was shocked at how much you reminded me of a hippopotamus. Only they smell much better than you do if you ask me. _

_ Or what about these words…"college graduate". Those two words will never ever be spoken in association with you, unless they come after "Russell is not a". You will be lucky if you make it through middle school, because you sure won't pass high school. With an IQ as low as yours? You'll drop out and go spend the rest of your life scrubbing bathrooms at burger joints, and making barely enough money to survive. You don't have the brains for school. And like I've already said, you don't exactly have the good looks to compensate…_

_ Oh! I've got another perfect word for you… "Loner". That's how you'll spend your whole adult life. __Because really, who will ever two craps about some smelly guy who's mean enough to pick on kids four years younger than him for kicks? So o_nce you're puny brain has admitted defeat and you've dropped out of school, there will be no more pansy kids to pretend that they like you because they're scared you'll beat them up if they don't. They will all throw a big party once you've left, and then they'll go on in their lives to have lots of friends, and later families, and they'll all enjoy each others' company. But you won't have left anybody to care you even exist.  


_ So I guess I am a bit sorry. I'm sorry that your life is gonna suck so much. Because if you were to ask me, I'd have to say the real freak here is you. You are a dirty, stinking, stupid, loser with no future, no real friends, and no value. Now tell me, which hurt worse? My first breaking your nose or hearing the truth about what you've got to look forward to in life. Personally, I'm just grateful Mrs. Timbers had me channel my angry feelings in this more appropriate way. It's really rewarding to have had the chance to verbally abuse you too…_

_ I guess the moral of the story here is pretty straight forward… Don't mess with my little brother. He's not a freak. You are. And I'm the pissed off older brother who will completely destroy you both physically and mentally if you ever make him cry again. Got it? Good. _

_Sincerely,_

_Dean Winchester_

**Secondary Author's Note: Thanks for reading! Please do keep the reviews and requests coming! They are the fuel for this series. :) **


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